If you look at the big things that could break in the next 5 years that wouldn't be due to natural causes like hail, you might want $10-$15k in an account to start out with that is available IN CASE something goes wrong before you have brought in a decent amount in monthly cashflow to build up a reserve account. 

You still can’t evict without just cause, but you can raise rent to market leveled.

Before you DIY this check with your insurance company this is not going to cause some exclusions in coverage. 

I'm worried this will cause a large "increase" in income for 2017 and a large "loss/deduction" in 2018.

(about 1/4 the way through both) Im hoping to find some answers in here to my concerns but i haven't quite hit them yet.So I thought I would ask... 

do some or all of the above places i mention give cause for concern?  

I know some of the mechanics are old and will need to be replaced soon, I’m just concerned about a city inspector coming in and making me do costly updates right off the bat, which would cost over $50k easy. 

Keep a collage and send it to the seller and express your concern about the deteriorating condition of the house. title insurance has nothing to do with this. 

We are probably making the same point but I said you could objectively compare travel habits, and that was listed first cause it is foremost in my mind.

Or you are concerned as comingling the personal asset?