In your case the numbers are not yet nailed down, but once they are, let those numbers (and remote property management figured into those numbers at 10% of rent) make the decision.

In any situation, if the numbers work in the end - it really doesn’t matter where, given the neighborhood you are investing in is reasonably safe.Once you’ve nailed down a location, you should make contact with a few PMs in the area - this is crucial for out of state investing.

There were a million nail holes to fill and cracks in most of the walls to fill.

I have a really little one (great for finishing nails but slow for framing), and my dad has a big one, but dad's is not portable like mine.

Putting up cheap paneling (and for some reason it's always DARK paneling) to cover plaster walls since these walls tend to crack easily with any nails is something I've noticed in many of the old houses around here.And yes, there are typically lots of surprises when dealing with an old house.  

@Ryan Moyer hit the nail on the head.

@Michael Mejia you nailed it with your last response. 

@Joshua Strickland and @Luke Carl nailed it on the head in my opinion. 

How much do certain mom and pops (nails, barbers, etc.) in similar properties pay?

My lease is fairly comprehensive and among other things, it explicitly prohibits nailing and drilling into ceiling joists in unfinished basements and garages.