Ultimately pick the town that will be most friendly/forgiving toward this style of housing. 

Buying a turnkey on your first purchase doesn't teach you much and I would argue you are overpaying in many (not all) cases).

In the perimeters of a Limited Action, I'm not sure you can claim punative damages there either.For the uninitiated, Punative Damages is a fine assessed by the magistrate and awarded to the plaintiff to teach the offender a lesson.

I know you said you are not handy, but I bet you could handle painting and google can teach you a lot to DIY.

Currently, I have 3 deals going:1) A gut job remodel turning a 1500 SF 3/1 farmhouse into a 3/2 rental with either a carport or garage. 2) A house hacking (my family's current residence) remodel of a 1700 SF ranch style 3/2 into an open floor plan. 3) A mobile home (currently shopping for a deal) rental on an empty lot with a septic tank and electricity already available. 

You need to look at properties within a reasonable range of square footage, same style, similar fixtures and finishings, similar lot sizes, etc, all within six months and within a half mile of the subject property.

There are far too many variables to consider when comparing houses in multiple neighborhoods, namely location, comps, future equity, type/style of home, etc.

Young professionals want this lifestyle in a new building with a gym and pool rather than the older style NYC living conditions in run down apartments with no dishwasher.

Can she teach my wife to tell me "Get out of the way so I can make more money!"

With section 8 you need to be aware that it will involve a more hands on management style.