And an actual lot split which was a SFH on .85 acre now turned into two separate lots, with a duplex on each lot.

Since you're open to markets beyond NYC, you might want to connect with local investor meetups or REI groups in those areas to build relationships with agents, wholesalers, and lenders who understand the nuances of each market.If you're looking to break out of analysis paralysis, maybe start by narrowing down one or two target markets and running numbers on actual deals.

The equity is actually what you are paying for the property. 

So this would actually work against the intended purpose. 

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.

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.

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. 

Is that aligned with what's actually out there?

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