I like the strategies of either seller financing (as much as possible), OR raising minimal debt/equity capital for your business in conjunction with private loans.  

If your goal is to minimize chaos, go with whichever option allows you to include a property manager in your budget. 

When appraisers value real estate they look at recent sales activity (within 12 months) of similar houses in close proximity and typically the most recent sales are the best indicators of current market value.

Real suggestions on how to minimize or eliminate taxes.Also the cost needs to be reasonable. 

As the investor/middleman in a sandwich lease your goal is to control the property with minimal cash out-of-pocket. 

Only you can answer that.You would want to look for KEY INDICATORS of what they are doing today and in the IMMEDIATE past to see current trending patterns.If something happened way in the past ( some call it young and dumb incident ) and it was an isolated incident then risk might be lower.If tenant demand is super strong for the area then maybe you do not have to take on a tenant that leaves you questioning whether to rent to them or not.No legal advice given. 

No theft, minimal liability, minimal valuation.      

It's a gauge of how prices have been based on recent transactions (i.e. as indicated before, it is the prevailing investors' sentiment). 

He then let me know that no obvious sources of a leak are known of in the home and no evidence of leaking is happening, but the high water bill is an indicator of a leak somewhere.This brought up a fundamental question that I wanted to put out to you and learn from you on:  if the tenant pays the water bill (it is in their name with the city) and there is  SUSPICION of a leak, who's responsibility is it confirm (and pay the fees that would be associated with confirming and/or finding the leak)?

Although i believe if you're completely new and plan on contracting out most of the work, its more important to study the areas, network and vet your people than to worry about the WHERE - theres certainly upsides for focussing solely on markets outside your own, its certainly doable and a lot of people do it, even (or maybe especially) when your starting out, the added risk can be minimized and downsides you cant eliminate may be worth the upsides.