Too much hassle. there are very few banks that will do an actual fix and flip loan and unless your a premier client of the bank the rate will be higher think 6 to 8% apr IF you can get them to loan on fix and flip which I am quite certain 95% of borrowers and a 100% of new investor / flippers cannot get. this is why HML companies have sky rocketed the banks left this space in the GFC and have not returned.. unless of course your a 1% er.. 

Am I thinking about this wrong or does it make sense to take this area and turn it into another 300-400 sqft of indoor livable space?

Repairs and improvements included side porch addition + converting/adding addt’l 400 sq ft from garage to rec space @ $60k.

Then you can start by reaching out to people in your network meanwhile building your credibility in the space by starting a thought leadership platform.

How long do you think to rent 40 spaces once developed?

We have a full size bed in the Hamptons at $500+ per night >200 sq ft space. 

However, in this day and age of the house hack, especially in areas where living spaces are hard to come by, why store your car in the garage when you could rent that puppy out and generate some cash flow?

There is a support beam needed under the enclosed porch which has been approved for interior living space.

My question is, do I bulldoze the garage and just use the empty space for parking?

Lending is such a dynamic space right now that changes on a daily basis.