This past winter i signed a tenant for three months with options to extend monthly until spring summer.

To prevent any future misunderstandings, simply inform them that paying upfront for an extended period is not feasible.

No one that I know of (ever in 33 years) will lend based on the ARV over Cost over that first short period of time. 

@Michael SoukupVA loans are for primary residences with a minimum occupancy period of 12 months.

We've had some of them take units for longer periods and just stay there the 7 days that they're in town.

Your agent should have advised a due diligence period to review info on leases, security deposits, rent history, etc., and that one unit would be vacant by closing if using an owner occupant loan.

After the 3 year redemption period you need to do noticing, file law suit, get a judgement but instead of taking ownership of the property like you do now, the new system will cause it to go to a tax deed sale to the highest bidder.

Period.

As you write checks and make deposits your income tax return is preparing itself.At the end of the tax year print a simple Profit and Loss report for the time period and hand it to your bookkeeper or CPAYou still need to keep receipts for seven years or so but the works does itself as you write and code each check.Even if you file as an LLC, Partnership or corporation your CPA will thank you.

On the flip side, multiple MTR/STRs in other areas could yield higher cash flow, especially in tourist-heavy or affordable markets, but managing dispersed properties can be challenging, with considerations like vacancy periods and potential property management costs if you opt out of self-management.