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.

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

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.

HELOC rates are high right now as well, which most lenders would not give the full amount anyway (maybe $15,000-$20,000 max in a credit line) which would leave your only option to be FHA anyway and still be tight as your DTI would increase more based on that.

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

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.

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?

The main thing being: giving up a property that appears to have appreciated pretty well is just a touch pill to swallow and I've regretted a few moves I've made when put in a similar situation to yours, and I had less equity in mine.It sounds like you're moving to Raleigh in the near future and want to buy a multifamily to househack.

If there are lease violations, mention them-you not having a key to access the unit WITH proper notice or in case of emergency is one of them.I'd also tell the tenant that they are clearly not happy there, so finding a new place is in their best interest as well and as they have several months, they should have lots of options.

Quote from @Stacey Wells: Hey everyone,I’ve been researching different funding options for real estate investments and business expansion.