Airbnb customer service rocks and I am a huge fan of Aircover! 

Is it usually a 6 month seasoning before being able to go for new appraisal and getting financed based on the ARV rather than cost.I've done a lot of reading and from what I understand this is possible, just looking for verification, recommendations on path forward or alternate plan, and also some lender referrals for when this takes place. 

If you are looking for true private money (no broker fee or points) most will not lend at a high leverage. 60-65 LTV max Now if you have experience, plenty of reserves, and the deal can be 100% financed based on the ARV, then you can present it to a hard money lender and they may feel comfortable doing it. 

Commercial real estate are not based on comps, but on Net Operating Income and Caprate.

Based upon your post the Greater Boston area and markets even slightly outside definitely seem to fit what you are looking for so just wanted to see if there was something you were considering as a negative factor.. 

Right now we have 2 units that are vacant, ready, and being marketed, and with the 'asking rent' reductions we just did to try to fill them faster (it's offseason for leasing), the estimated market value of the building based on net operating income is now $1,542,500.

Just trying to get a better understanding of the type of policy/agreements I need to cover all bases. 

I am a huge fan of St Pete and that's where I would live if I had to move out of Fort Lauderdale.

Look for equity growth and purchase based off total ROI not just cashflow.

@Nicole Lane Love the idea and I'm a big fan of tiny homes myself, and have looked into some options on some of our props in a couple states.