Start a time log today.Change no other habit.Get out of bed at your normal time.Shower.Brush your teeth.

That would be the first question to evaluate.

I think you should evaluate what your minimum needs are and downsize to the smallest place you can and start to build some reserves.

Have it independently evaluated as Scott mentioned.  

I used Buildium where I used to be affeliated, and I liked the fact that everything was online, maintenance requests were tracked from start to finish, and tenants could log in pay rent online as well as their trouble  tickets.  

I have over 50% equity in my current home (300-350K equity).I am trying to evaluate if it would be wise to sell the primary residence and put the cash in to out of state properties (with leverage, operating a million $ investment with 20-30% down).That could generate enough income (and more) for me to rent a 4 bed home that will suit my family needs.  

I would walk them, drive them, evaluate what the standard home in that area usually sale for, rent for, and what is the standards for that area(amount of bedrooms, baths, square footage, years built).  

The bank will take a timber deed or assignment of my logging contract along with a UCC filing.3.

The entrance to the downstairs unit is via concrete steps at the rear of the house.Are there any special considerations I should make when evaluating this property?  

I imagine your run-of-the-mill Inspector would be able to evaluate the problems with the property better than your run-of-the-mill GC.