If it was unforeseen medical debt, and you've made progress in straightening things out, you might find a private lender to work with you for an eye-wateringly high interest rate.

TIAErich your best bet would be to amortize it over thirty with a 5 year balloon. the issue with private lenders  vs. banks is private lenders use their money to lend and many times it may not keep up with inflation - so lending for that long does not make sense.

This could be anything from confusing UX to lack of certain integrations.How useful would a custom listing site be for you?

He is "the" KGB master strategist, what he was able to achieve through strategy and guise is only paralleled by Adolf Hitlers rise from private in a jail cell to Fueler. 

STRs sound like too much work to me.Portfolio income = stock dividends, interest income (from banks, credit union etc), Master Limited Partnerships (Form K-1), Business Development Companies (Form 1099), bonds, interest earned from investing in a real estate debt fund, interest earned from being a private lender

I'm looking for ways I can "protect" this private lender. 

So it isn't a complete waste, you would simply need to follow the strict reading of the law with no private clauses for consideration...I'm not sure how that plays out since technically if the lease is void, so is the tenancy meaning you could terminate anytime and not wait for the original lease expiration...I'm sure that's covered somewhere, but again I'd ask my local atty what to do given this is such a locally specific issue. 

Just giving out free stays near yearend will not help in maintaining customer stays.

I have done Private Money Loans on auctions in the past.

Remedy after termination.If the rental agreement is terminated, the landlord may have a claim for possession and for rent and a separate claim for actual damages for breach of the rental agreement, reasonable attorney fees as provided in § 55.1-1245, and the cost of service of any notice under § 55.1-1245 or 55.1-1415 or process by a sheriff or private process server, which cost shall not exceed the amount authorized by § 55.1-1247, and such claims may be enforced, without limitation, by initiating an action for unlawful entry or detainer.