So if you have a policy that says you wont rent to applicants with prior evictions then you hold to that. 

The holding costs for the time it takes to get permits and build especially if you are not doing this with cash (which almost nobody is) are enormous.

Keep researching, but don’t let fear hold you back—small, intentional steps add up!

So I would separate the days you want to enjoy it for yourself and if they're already booked, you hold every right to cancel them as long as you provide timely notices, full refunds, maybe even a slight discount for other dates, etc.

These all require applicants to submit an acceptable Letter of Explanation addressing each specific issue and occurrence.Rental HistoryBecause a current landlord may say anything to get rid of a bad tenant out of desperation, we also require information for the previous landlord of all applicants…Analyze IncomeMany landlords require a month of paystubs from applicants and just use these to calculate a monthly qualifying income…Employment StabilityUnless an applicant has exceptional credit, we strive to determine their stability of employment…AssetsWe are one of the few management companies that requires a bank statement as part of our application process…Letter Of ExplanationAny time there are credit issues or we discover an inconsistency, we require a written letter of explanation (LOX)…UnderwritingTraditionally, landlords have only looked at the income of applicants…ApprovalOnce an applicant is approved, we require a nonrefundable Holding Fee to make sure they are serious…

No, you cannot create phantom losses this way.Some additional issues that we have not addressed:- holding rentals inside an S-corp has many tax disadvantages- you will likely jeopardize your $250k/$500k capital gain exclusion for homesteads- you will lose asset protection afforded to personal residences by most states- you will lose your homestead exemption for local property tax - your insurance will have to change from owner-occupied to rental, i.e. go up- and there's moreConclusion: there're reasons why nobody is doing this clever "strategy" but A+ for trying.

Investment Info:Condo buy & hold investment in Fairbanks, Alaska.

.🎯 The Buffett Dividend Strategy Coca-Cola remains one of the best examples of Buffett's philosophy in action:1988-1989: $1.3 billion investmentHeld for 30+ yearsGrowing dividend income streamShows the power of buying quality assets and holding for cash flow💳 The American Express StoryBuffett began buying AMEX in 1964 during the "Salad Oil Scandal" crisisMade a larger investment in 1991Berkshire now owns about 20% of American ExpressThe investment has generated billions in dividend incomePerfectly demonstrates Buffett's principle of buying great companies during temporary troubles (just like smart real estate investors who buy in good areas during market dips!)

I hold licenses within real estate, insurance and securities for this very reason.

A well-designed space becomes a vacation destination in itself—one that holds its value and stays booked long-term.