Also another thing to consider are most municipalities will significantly increase your taxes if you pop the top of the house.

The property looks fantastic and is in a great area! 

If you are not on top of so many things it a great chance you can lose.

The smart play would be to build a two story wood frame structure on top of piers or concrete block in most cases. 35 feet is a pretty typical height limit in most neighborhoods, so depending on elevation you SHOULD be able to build two stories on top of the elevated foundation.

There are a few questions off the top of head. 

Weird they charge a $75 fee on top.

@Liam Alvarez  I've never seen an app or a website that analyzes all markets and spits out the top 3 you should invest in for the highest returns. 

Reason, if the individual is willing to give me top dollar rent and thinks he can still make a profit, then it's a win/win.

If I were you, I would arrange to have your materials removed before they get there to work because city guys are pretty rough on stuff they have to move.We occasionally found issues like the corner of houses built in the easement and sometimes on top of a water or sewer line.

This of course depends on your starting bank roll - but if its like mine (under 100k) - Im trying to put as little as possible into it on top of initial equity and fees.this will likely chew a big hole in your ROI  (now if you are looking to improve value with a cash out refi or a great prospect comes along that needs combo new plumbing, roof, windows, foundation repair, etc - well just make sure you know what youre getting into and/or have a good contractor and finger on the pulse of the market when estimating the ARV YOURSELF - couple missed items and you risk having a bad first investment and not doing it again).    7) dont be scared be ambitious ( i should heed my own advice sometimes) 8) define numbers goals within your target areas.