I am fairly confident that just the front unit alone will appraise to the sale price.Main problem I have right now is the legal issues with unpermitted units.

Do not rely on it for legal advice.

Your situation (different country, Airbnb income, longer hold time) may not fit this model exactly.Negotiating Better Terms:With the bank: Shop around for better rates, consider a larger down payment for better terms.With real estate agents: Offer exclusivity for a lower rate, or consider handling the sale yourself if legal in Georgia.Holding Period: Given the strong Airbnb cash flow, holding longer could be beneficial, especially if the market is appreciating.

Maybe the current tenants don't care, but if they are also below market rents and you start bumping their rents, will it be opening the door for more complaints or increased likelihood of them leaving because they are being impacted by the smoker.  

If the later is the case, unless your contract with that buyer had specific performance language in it, there is nothing you can do.As to the advice above about potentially clouding title, you are now entering the legal realm and you should NOT be taking legal advice from anyone other than your attorney as clouding title in THIS case can swing back at you from the original sellers for not performing and claiming damages against you.If you intend to wholesale, you need to do it legally and ethically and in many states, that requires either a license, closing on it with your funds or borrowed funds, then marketing for resale once you have title, or having your buyer upfront, forming a legal entity with both you and buyer as owners.

I was going to draft up one contract with each LLC as a separate "Owner" with the authorized representative for all, the actual owner, to sign the one contract for all legal entities, but they didn't like this and want to keep all documents separate.I gave them a VERY competitive price quote based on the total portfolio as 1 account with the total number of units.

Fiduciary responsibility could be in question if a deal closed and the apparent goal is proposed by some legal team that it was mostly done to not lose a large nonrefundable earnest money and/or to get a quick pop of ca$h on an Acquisition Fee.

Respectfully,Zach The best bet is likely to create a new LLC that lays things out in a straightforward but legally strong and standard operating agreement, etc. - LLC doc sets are fairly cheap and easy to create these days (with limited assistance from lawyers) and its much much better to have that cover bases on arrangements like this - it will also fit nicely with financing options - whether you take on debt from a lender in a co-equity situation like your first plan (refinance loan to LLC post rehab?)

I know Massachusetts doesn’t like landlords that’s why i am a bit hesitant to take legal action.  

If you act as a consumer and unless any of the legal exceptions apply, you have rights to cancel the Subscription Listing Fees during the cooling off period.