For me, the first pass at underwriting is simply about determining if a deal is worth exploring further.In the current market, I’d say 9 out of 10 deals are dead on arrival.

Raising money is all about marketing and sales (not real estate specific) so either hire marketing agency and read sales books, or hop on some LinkedIn courses on marketing and sales.Not sure the legal structure to use: talk to accountants and attorneys.Need deal flow: talk to brokers and go to a lot of networking events.Lending terms: start calling banks and loan brokers.From there, it is all risk mitigation. 

Hey GaryI manage about 65 units in FL and I broker for STR buyers in this market, and some do self manage.Obviously the ones who choose us for management, we can assist with all of those items, but the ones who self manage do so by building a team. 

I'd recommend looking at costs. your build cost is going to be well over other homes because of the fixed costs like slab, Hvac, roof, etc. check the market drivers and weight the benefits of short term versus long term. long term is no furniture and help pays mortgage but at this size it doesn't really cover everything. we didn't find a lot of economies of scale in single family detached. can you build more than one unit?

Study the market.

In my market the valuation with f/f non commercial financing is typically lower than the hands off cost of adding the ADU.  

The rental market has slowed in recent months but expected in winter.

Those states could be nearby in your market area.  

This last year I've been trying to really learn the business and begin to market for properties.

There aren't any good wholesalers in the Cleveland market.