I'd pivot the condo to a SFR in the Boston-area, but really analyze if your vacancy is prompting you to transact, then are you really fit to invest?

Consult a real estate attorney and CPA to finalize the LLC structure and ensure the transaction, tax filings, and ownership terms comply with state laws and IRS regulations.

HOWEVER - it may be difficult for the appraiser to access the true value if a large percentage of transactions are not in the MLS.  

Alternatively, you may want to consider switching to a platform that offers this level of transparency.Additionally, on both Airbnb and Vrbo, if you have access to the account, you can view the transaction history.

For a number of years I've formed transactional partnerships (form an LLC with single or multiple members to buy a building, build condos, townhomes etc).

Most transactions between friends or loved ones fail.

Many people choose NOT to have this, because the administrator will then vet every investment you make to ensure you do not invalidate your IRA.Invalidating your IRA means that you've done a prohibited transaction and the entire account is then deemed as distributed to you.If you don't want checkbook control, then I recommend a plan administrator such as Equity Trust - www.trustetc.comIf you are sure that you're aware of all the rules around prohibited transactions and disqualified people (who you can and can't do business with), then a plan administrator like Sense Financial would be a good place to start talking.  

The transaction dragged on for months and months.

These will put pressure on a simple Wholesale transaction.

Just about every time I have been privy to the details of a transaction where one of the parties is unrepresented and the other is, the unrepresented party gets the short end of the stick.