BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

Today, that building generates enough passive income to cover his annual retirement contributions.You mentioned taking the 10% penalty, which I’d only recommend as a last resort.

I'd recommend checking out the Midwest market.

I would recommend keeping them, and gradually increasing rent on par with market increase + 1 to 2%.You could get a better qualified tenant, but they could be worse with money management, property respect, etc.

Thanks in advance for the recommendations / suggestions!  

Any recommendations for finding a coach would be greatly appreciated!

I recommend you include some of your key qualification criteria in the advertisement.

Generally we raise capital from investors who want a fixed income and have enough meat on the bone to keep all the equity in the deals and push the valuation and also obtain commercial financing where we can get 75-80% LTV financing and still maintain a DSCR of 1.2+2.) 

Can anyone recommend some companies with a track record like Praxis?

It's a big decision, and I recommend spending some solid time in each area.