I'd also recommend dumping the garages there's almost a total loss on that unless you are putting units above them on a dense infill lot for additional units it's not worth the cost of construction. build cost is pretty high for your market for three story suburban walk ups. we could never build at that price and make any money. suburban sells for 160k a door in our market with land. get on yardi make sure you Arne't going to lose money on it.

How ‘hot’ is the market?

If you had a bit more capital, say $80,000 - $100,000, you could start doing BRRRR's in markets like Detroit (this is what I do).

Looking ahead to my next project, do you have any advice or resources for finding off market deals? 

I've been looking at some of the online lenders (Better, Figure, Rocket Mortgage, etc) and while they offer a decent product, perhaps there is a lender who is local to Indiana that would offer a HELOC with better terms? 

I'm eager to learn from your experiences—what strategies or processes do you use to determine expense figures in your market?

The market is very tight at the moment, but there are still opportunities to be had!

With the season in Sarasota County considered November - April, what is the best way to market the property as a Medium Term Rental (at least 30 days)? 

Make sure that the market there makes sense for your goals to invest.

I've noticed in my area that houses that have been converted into 2 units tend to sit on the market for much longer and sell for much less than traditional single family houses with similar sqft and finishes.