For long term holds I like upward transistional neighborhoods where I can see future forced appreciation while the asset cashflows. 

Have I crossed over to an unhealthy obsession??? 

I hired a surveyor to do a site plan, which he did and which he stamped.

The best thing you can do is to work with a realtor / property manager who's experienced doing Section 8 rentals and have good contacts over at CMHA to help you when issues inevitably come up.The process can sometimes take 2-3 months, but there are other programs like EDEN that can go a lot faster. 

I was hoping to structure a deal that involves paying the seller every month and then a balloon payment in 5 years (when I can get an 80% LTV cash out refinance to put a mortgage on the property without having to put any money down because I'll have built up at least 20%).

I am debating whether i should just fix the shower pan. or, rebuild shower as well just in case water leak is coming from shower walls. what do you think? 

I appreciate the offer to call for me, Will, but I can do it.

I have a rental property that has a main house and an ADU on it. 

I have a few questions for my fellow investors:What tools do you currently use to evaluate your deals?

Not sure I can do that on three acres.