Covest STR Investing — Answers
Every real question investors ask before getting started with Covest, Colorado's full-stack short-term rental brokerage — ownership, fees, underwriting, financing, taxes, management, and more.
43 questions, answeredOwnership, Structure & Fees
Do I own the property outright?
Yes — 100%. You purchase the property in your own name (or your LLC). Covest LLC represents you as your licensed buyer's agent, and Covest Setup LLC handles furnishing and design under a separate post-closing contract. You hold clear title from day one.
How does Covest make money?
Covest LLC earns a buyer's agent commission at closing, negotiated and disclosed upfront in your Buyer Representation Agreement before you're ever shown a property, as required by Colorado real estate law. This is typically 3% of the purchase price and in many transactions is offered by the seller, though always transparently disclosed. AirSimplicity earns a management fee on ongoing rental revenue. No hidden fees.
Can I use an LLC or entity to purchase?
Yes. Many investors purchase through an LLC or other legal entity. Covest works alongside your attorney and CPA to structure the acquisition correctly, and can provide referrals to real estate attorneys familiar with Colorado STR ownership structures if needed.
Is there a cost to talk with Covest before I decide anything?
No. The first call is a no-obligation conversation to see whether Colorado STR investing and your goals actually line up. Covest only earns anything if and when you close on a property through them as your buyer's agent.
How Covest Underwrites & Evaluates Deals
What does “AI-powered underwriting” actually mean?
Covest has built proprietary tools that pull occupancy, revenue, and booking data from multiple STR data platforms and layer in real historical portfolio performance data. This models realistic revenue projections — not optimistic estimates — before an offer is made. Learn more about how Covest evaluates markets.
What are realistic returns?
Portfolio properties have averaged double-digit cash-on-cash returns in year one, depending on market, property type, and financing. Covest shares conservative, data-backed projections rather than best-case scenarios before any purchase.
What happens if a property underperforms my projections?
Underwriting is built to be conservative specifically to reduce this risk, but no investment is guaranteed. If a property underperforms, AirSimplicity adjusts pricing and marketing strategy based on real booking data, and Covest stays involved past closing rather than disappearing after the sale.
What are the biggest risks of STR investing?
The main risks are regulatory change (a market's rules shifting after purchase), performance risk (bookings coming in below projection), and the general risks of real estate ownership (maintenance, market value fluctuation). Covest only works in markets with stable regulatory environments, underwrites conservatively, and uses professional management to protect performance — but this doesn't eliminate risk entirely.
What if Airbnb or VRBO change their platform policies?
Properties are listed across multiple platforms simultaneously — Airbnb, VRBO, Expedia, Marriott Homes & Villas, and Google — which reduces dependence on any single platform's policy changes. AirSimplicity actively monitors platform-level changes as part of ongoing management.
The Buying, Renovation & Setup Process
What if the property needs renovation?
If construction work is required, Covest Setup LLC coordinates with a vetted, licensed local general contractor and acts as the design lead — selecting finishes, tile, fixtures, and layout. You're not managing the renovation yourself.
Do I have input on the interior design?
Yes. Covest Setup LLC leads the design using data on what actually performs for STR guests, but this is collaborative — you're not handed a finished product with zero input, though you also don't have to manage the process.
How much does furnishing and setup typically cost?
This varies significantly by property size and condition, and is scoped individually as part of your specific deal rather than a flat number — it's discussed and budgeted before you commit to a property.
How long does the design and furnishing phase take?
Typically 4–8 weeks, as part of the overall 3–6 month timeline from first call to live listing.
Does Covest check HOA rules before I buy?
Yes — HOA rental restrictions are underwritten before a property is brought to you, since a town STR license means nothing if the building's own HOA prohibits short-term rentals.
What happens on the first call?
A direct, no-obligation conversation with Shalom to understand your goals, budget, and timeline, and to see whether Covest's model fits what you're looking for — not a sales pitch.
Financing & Getting Started
Can I finance the purchase, or does it need to be cash?
Financing is common among Covest investors — this isn't a cash-only model. Being pre-qualified (or willing to get pre-qualified) for a loan is strongly preferred before actively looking at properties, since it affects what's realistic to target.
Do I need a lender lined up before my first call?
Not necessarily, but you'll want to be in the process of getting pre-qualified relatively early, since financing terms affect what properties and markets make sense for your numbers.
Do I need real estate investing experience to work with Covest?
No. Covest is built specifically for a hands-off model — the value is in Shalom and his team handling the market, deal, design, and management work, not in you already being an experienced investor.
Management, Guests & Day-to-Day
Is this truly passive?
Yes. Once you close, Covest Setup LLC handles setup and AirSimplicity manages operations — guest communication, cleaning, maintenance, pricing, and reporting. You receive monthly statements and cash distributions. That's it.
Who manages the property after I close?
AirSimplicity — a Colorado-based short-term rental management company co-owned by Shalom Kaiser and Jonathan Scheiner. AirSimplicity manages Shalom's own personal STR portfolio too, has achieved Airbnb Superhost status, and actively manages pricing, guest communication, cleaning, maintenance, and monthly reporting across every major channel.
Why AirSimplicity instead of another property manager?
Most property managers use off-the-shelf pricing software and treat a property like a number. AirSimplicity's leadership are active investors themselves with skin in the game — Shalom's own portfolio is managed by the same team, at the same standard, as client properties.
How are guests screened?
AirSimplicity handles screening as part of day-to-day management, using the verification tools available through Airbnb, VRBO, and the other listing platforms, alongside their own operational standards as a Superhost-level operator.
What happens if a guest damages the property?
AirSimplicity handles guest communication and any damage-related issues as part of ongoing management, including working through the relevant platform's protections and any applicable insurance. This isn't something owners are expected to handle themselves.
Who handles emergencies or maintenance issues?
AirSimplicity's in-house team handles maintenance and guest-facing issues directly — full-service management means owners aren't fielding a 2am maintenance call themselves.
What platforms is my property listed on?
Airbnb, VRBO, Expedia, Marriott Homes & Villas, and Google — managed centrally by AirSimplicity rather than requiring the owner to coordinate multiple listings.
Does AirSimplicity only manage Covest-purchased properties?
No — AirSimplicity manages Shalom's own personal STR portfolio in addition to Covest client properties, which is part of the alignment Covest points to: your property is managed at the same operational standard as the founder's own holdings.
Money: Distributions, Taxes & Comparisons
How often do I get paid?
Investors receive monthly statements and cash distributions from AirSimplicity, based on that month's actual booking revenue minus operating expenses and management fees.
When do I start seeing income after I close?
Income starts once the property is set up, furnished, and live on booking platforms — which, combined with the closing timeline, generally falls within the overall 3–6 month first-call-to-first-booking window.
How are short-term rental profits taxed?
STR income is generally treated as taxable rental income, and specific treatment (deductions, depreciation, entity-level considerations if purchased through an LLC) depends on your individual situation. This is general information, not tax advice — Covest can refer you to a CPA familiar with STR taxation, the same way it can for real estate attorneys.
Are there tax advantages to buying through an LLC?
This depends heavily on individual financial situation and state-specific rules, and isn't something to decide from general information — it's worth a direct conversation with a CPA or tax attorney before deciding on entity structure. Covest can provide referrals if needed.
How does STR investing compare to a long-term rental?
STR properties in strong markets can generate meaningfully higher revenue per property than a comparable long-term rental, since nightly/weekly rates apply rather than one flat monthly rent — but that comes with more operational complexity and regulatory exposure, which is what Covest's underwriting and management model is built to absorb on the owner's behalf.
Markets & Regulatory Risk
What markets do you focus on?
Exclusively Colorado. Primary targets are the Denver Metro area and markets within roughly two hours of Denver with investor-friendly, unrestrictive STR regulations — including the foothills communities (Evergreen, Conifer, Bailey), Summit County (Breckenridge, Keystone, Copper, Frisco, Dillon, Silverthorne), Grand County (Winter Park), and select mountain towns along the I-70 and Highway 285 corridors. Covest does not invest in markets with burdensome permit caps, owner-occupancy requirements, or hostile regulatory environments. See current market breakdowns.
What if STR regulations change after I buy?
Regulation risk is real and one of the core reasons Covest is selective about markets. Regulatory trends are actively monitored in every market Covest operates in, and only markets with stable or investor-friendly policy environments are recommended — regulatory scenarios are factored into underwriting, though no investment is without risk.
Selling, Exiting & Multiple Properties
Can I sell the property later?
Yes — you own it outright and can sell whenever you choose, the same as any other piece of real estate.
What happens to my management agreement if I sell?
Management agreements with AirSimplicity are tied to ownership of the property, so they generally end at sale (or can transfer, depending on the buyer's preference) — exact terms should be confirmed with Covest directly, since it depends on individual deal specifics.
Does Covest lock me into a long-term contract?
Specific contract terms (the buyer's representation agreement, the setup contract, and the management agreement) are reviewed and disclosed upfront before any commitment, consistent with Colorado real estate disclosure requirements.
Can I buy more than one property through Covest?
Yes — many investors build a portfolio of multiple properties over time rather than stopping at one, using the same end-to-end process for each additional purchase.
Who This Is For
Who is this designed for?
Investors who want higher returns than traditional long-term rentals or other real estate sectors, and who are comfortable with some creative deal structuring. Ideal clients are accredited investors or those with at least $200,000 available to invest, pre-qualified (or willing to qualify) for a loan, and who want to be hands-off while a seasoned operator runs everything.
How much do I need to get started?
Generally a minimum of $200,000 available for investment — covering down payment, closing costs, setup fees, and initial reserves. Being pre-qualified for a mortgage is strongly preferred. Full capital requirements are walked through before any commitment.
What if I want to use this as my vacation home?
That's completely fine — owners can use the property however they wish, and many investors block out dates for personal use. Personal-use days affect annual revenue, which can be modeled into projections upfront.
Can I invest if I don't live in Colorado?
Yes — most Covest investors aren't based in Colorado. That's part of the point of a fully hands-off, professionally managed model; there's no need to live near the property or visit frequently to own and benefit from it.
Do I need to visit the property in person before buying?
It's not required, though some investors choose to. Data, photos/video, and direct underwriting information are provided so a decision can be made remotely if preferred.
How long does it take from our first call to my first booking?
Typically 3–6 months from initial conversation to live listing — including market targeting, property search, offer and closing (30–45 days), and setup and staging (4–8 weeks).