--------------------------------------Context:-My wife and I file taxes jointly and own 4 long term rentals in NJ and 3 rentals in FL (1 long term, 2 short/medium term).

You must also vet the insurance agent, the RMLO, the 3rd party loan servicer - everyone.A well thought out medium between analysis/knowledge and using experts -- in my opinion -- is the best way to advance.Stay safeAlan

There is a big tree there, limiting the width of the alley to about 8ish inches.

Just buy and hold strategy for medium to long term.Cant do Forced value or any renovation.

I felt like I needed to "graduate" and we spent some time looking at medium size apartment buildings. 

Purchase price: $342,000 I do Airbnb on it, and medium terms.

They have to meet modern codes and SEQUA requirements.. this is what stops building on lots that would not be buildable with modern subdivisions map act standards or modern zoning. in the hilly areas road widths and slopes will not meet Sequa so they stop building on those lots there are thousands of the lots scattered around LA county and these are the lots you see going to tax sale all the time.

As a medium-term rental, you'd be in better position to be connected with Insurance Company that way.  

I found out in my jurisdiction that medium-term rentals are classified as long-term rentals and therefore have different laws.

5-year prepay often has the sharpest pricing, but, 3-years can often be a nominal trade off or happy medium.