More often than not you get a leak it adds a couple hundred dollars worth of sheetrock and paint work and you then repair/replace the roof but if you have delayed that maintenance for several years you are way ahead of the game.In my opinion, you immediately handle any maintenance that makes the place unsafe or uncomfortable to live in as well as any maintenance that will cause more damage the longer it goes. 

Since easy to commute, easy access to life style might be not so much important if work from home is more like routine choice, so maybe we should define A,B, C and D otherwise?

But we are routinely generating $30k to $50k profits per house.

Hey, if you feel the least bit uncomfortable, it is still your option to walk away as long as you haven't invested any money yet.

Also thinking I *might* be able to hold onto this as a rental in the long term if the numbers really make sense, but still really uncomfortable doing that knowing that I can't sell it to anyone but a cash buyer down the road. 

If you are in any way doubtful and feel uncomfortable, don't do it.

I have broken so many rules, some out of ignorance, many not.For instance, I have paid contractors an up-front payment before work is done.  And I've been taken.  But I also have a very reliable contractor that requir...

I would say if you've read J scott's book and are still uncomfortable, i would personally deduct an extra 5-10% to your best offer for wiggle room and make your offer, even though with his book and homework done on your area, you should be more than knowledgeable. 

@Christopher Phillips My gut told me these viewpoints would prevail, but I had been warned locally that "many contractors" would be uncomfortable.

You can always have a property manager take over at any time if you get in a position where you are uncomfortable.