You should reach out to @Melissa Haworth she can get the actual numbers/rents on STRs in the area to help run your comps.Each building is different, each area is different, it is important to find accurate data to make good decisions.

Assume that you're sitting on:$200,000 in suspended passive losses$150,000 in business losses$100,000 in expiring NOLsThe Magic Transformation:That $500,000 of "painful" ordinary income becomes your strategic advantage:Absorbs all $450,000 of those otherwise-stranded lossesLeaves you with just $50,000 net ordinary incomeMeanwhile, your §1250 gain still gets preferential rates:$581,820 at 25% max (unrecaptured §1250)$700,000 at 20% max (capital gain)The Plot Twist:What looked like a tax nightmare actually solved multiple problems.

Can I do it as an investment property first and move into it at a later date?     

I've actually started looking into that today, thank you.

The mechanics of the transaction were actually very involved and some of the most intricate and detailed of any transaction I've been a part of, however the results were worth the effort.

I had a client who actually decided to pursue converting the house to a boarding house to avoid any problems in the future.

Please let me know if you need more info to create a clearer picture.Thank you.That is actually a good question to get advice from a local estate attorney on.

(they're actually starting to slightly pickup).

I think it's actually super cool and unique to have a fireplace in an attic studio—definitely adds character, which is always a win for STRs!

@Robert Brock, I guess my advice is not really any different than I would say to someone wanting to be a residential wholesaler: you need to add value to the transaction.Often times, having the deal tied up is the value, but more often then not, in my limited experience with commercial wholesalers and residential, the wholesaler has no idea what someone will actually pay, so they tie up a deal at too high a price and then add their fee that turns a bad investment into a horrible investment.