You are trying to say you will use the " investors" to fund community programs, that sounds like a charity because there is no earning on the investment.  

A coach makes sense if you are 23 and want to increase your skills enough to earn a living with the sport.

(Side note:  I'm not happy that I know any of this...hard earned lessons of real estate investing). 

Ok, CASH.

We originally used an FHA loan with 3% down, took on MIP, and now have a $2,100/mo mortgage with $225 HOA/mo - so about break even on cash flow. 

They all cash flow and are easy to manage (so far).

Someone trying to earn 4-5% return they could get from a bank cd?

My plan is to mainly focus on cash flowing properties that make the 2% rule. 

If you're looking for cash flow you can easily make $300/mo net on a single family property in a better neighborhood/condition.

Understanding your top priorities can help in determining whether Stessa, Baselane, or another tool might best fit your needs.If you're comfortable with apartments.co for rent collection but want higher yields on your cash (this is me reading between the lines) you could have the transfers go into a high yield business account like BlueVine 1.5% interest or something like CapitalOne 3.9%.