Additionally, she is used to the lifestyle that my dad used to provide while he was still working and she currently spends about $6000-8000/mo (a lot of which is also medical expenses for chronic conditions), so she withdraws from the stock portfolios to supplement current spending.

2) I like the idea of a small team that plays off of eachothers strengths and covers the weaknesses where you can get input from more experienced profesionals but  also I can think of a bunch of reasons why taking on parters silent or not could be stressfull to say the least.  

We'd need much more insight into the OP's life, life goals, skills, strengths and weaknesses, investment objectives and risk tolerances before providing a real good answer to this questions. 

Most people are weak but you are strong because you have decided to take your destiny into your own hands.

My weakness is the financing, Knowing the various local markets. 

This has worked well, but we are adding more units so it will get harder to keep track of who got the waiver and who didn't, I will be doing away with the policy.In my experience, they are either paying on time, all the time, having an issue once or twice, or chronically late.  

I just thought I needed to get a little more education on ROI, since I am weak when it comes to that kind of math.

My weakness is that sometimes I come off to harsh, and I hate doing paperwork (though I am very organized I just don't like it).

problem with adding a booster pump on a well that has a weak pump or is low producing is you will cause the pump in the well to cavitate or short cycle .

This suggests the demand has been relatively weak.