@Samuel Coronado - the challenge is that there will likely be a very small number of renters looking for a house that size, as well as that can afford a rent amount that high who won't just buy otherwise. 

Well I think he was planning to pay it but it wasn't long overdue so he certainly wasn't expecting a lien to be placed on the house one day prior to sale.

Hi Joshua,It sounds like you’ve got a solid situation—congrats on positioning yourself so well!

Well, the latest "clarification" of the vague memo is that "rental assistance programs" are exempt from the pause - so I am expecting payments to arrive as usual.

If they are already asking for discounts, it doesn't bode well.  

I've brokered a number of 1031 transactions and can help with that as well. 

If you’ve got property and aren’t well-versed in an accounting software I’d recommend starting with a good accountant and quickly adding a good bookkeeper.

Over the 30+ years my wife and I have walked and pencilled well over a thousand possible deals. 

Without knowing all of your specifics, I'd say that it's only worth holding on to if you can reasonably expect to have some really good appreciation in the near future (like 5 yrs)....Or, in the case where it would run well as a vacation rental, you could switch the usage, maybe?

Selling to an entity you own and renting from yourself looks like a tax dodge to the IRS, and they’ll likely reject it.Better AlternativesIf you’re looking to maximize deductions, consider more straightforward strategies like:Renting out part of your home (like a basement or room) while still living there.Keeping clear records of home office expenses if you work from home.Investing in other rental properties that aren’t your primary residence.Michael Plaks explained it really well in his response.