These need to be keep separate for us to evaluate the deal. 

Recent events with my family made me realize I want to work to live and not live to work.Ultimately, I am looking to generate enough cash flow to retire in the next 15-20 years with progressively more freedom until that time to spend with my family.I am currently reading and absorbing as much as I can about REI.

It does not really affect me personally, but what if it starts with weed and progresses to hard drugs?

I had to get an engineer to evaluate it, and he found what was there was insufficient and i ended up having to reinforce the span significantly.

There are a thousand options...I would rather consider a stepped up progressive mortgage: i.e. start with lower fixed payments so you can fix this place up with the cash flow and increase the payments once stabilized...But it sound like there is quite a bit of deferred maintenance...how do you plan to cover repair and cap ex?...

If a new one cost $1,000 and had a life expectancy of 15 years, then I would divide $1,000 by 15 and charge them for the remaining year of life expectancy.To make a long story short, my recommendation would be to charge the tenant for the trip charge required for the plumber to come out and evaluate the water heater.

Here is my question for the community - what factors do you look at when evaluating the health of a market from afar? 

Efficient landlords know to repair and bill as the tenancy progresses to avoid major costs at turn over.

My question was more about taking into consideration all of those things you mentioned and analyzing the difference of risk involved, and how investors would evaluate or underwrite the deals differently. 

For the buy n hold investors, how do you analyze and evaluate deals?