I mainly need someone who can inspect the outside structural integrity (walkways, elevated porches, concrete, etc.) and the common mechanicals (i.e. boilers).

Might consider another room to exit and use a deck walkway to the main deck area, a pass through serving window might be handy.

I guess the bigger challenge for me figuring out which areas will attract the better tenants, even though it may cost me a little more to acquire a property, I am more comfortable working with a better class tenant, someone who would actually cut the lawn and clear their walkway, respect the property, and can manage to mail a check somewhere around the 1st of the month.   

My husband spoke with a lawyer who advised him not to do any repairs to the outside (the front walkway is not usable at all so she cannot use the front door, house needs painting, etc) until she is out.

We had a drive and short walkway added last week.

That just doesn't work and some just walk way.

Here are some additional things to check for from an Insurance perspective:- Knob & Tube or Aluminum wiring- Asbestos tile, siding or wrapping on pipes- Lead paint (if the building was built prior to 1980 you may need a Lead Safe certification)- flat roof- tenants with pets (find out breed of dogs)- cracked or damaged driveways or walkways- Stairs with out handrails- trees over hanging the property- in ground tanks (active or inactive)- two means of egress from all units- if smoke, CO, fire detectors are hardwired or batterySome of these will cause insurance companies not to write the coverage while others may turn up as recommendations that you will have to fix.   

What happens when it needs a new roof / walkway / HVAC / tax increase / etc? 

Since it's worth $1.3 million and she bought it for $550,000 and she owns it now with no mortgage, It sounds like she needs to calculate if she (or they when they get married) walk way with more proceeds from doing a 1031 exchange and the depreciation recapture vs. using the $500k exclusion for primary home owners)?

When I visited to take photos recently there is a small deterioration to the walkway at the end but its no different than any other crack you might see on a city sidewalk.