Also get multiple bids for ur floors cause as a small retailer I can beat Lowe’s and Depot on price and install.

It's just for show, as far as these guys are concerned, the money belongs to the rich co-workerSo it all depends on your personal situation.It's funny that the bank made all this fuss during the qualifying stage, but at the closing, they don't check or care to see where the funds came from.

Never late in 5 years, never any major concerns at the property or anything.

There are several legal concerns with your proposed business model which should be reviewed by a local attorney before you begin leasing.

The bigger concern is that between ALL the ways in which they take a bite, their bite was about 20% of the rent. 

Also, will I be able to sue the squatter for the back rent that I could have collected and damage caused to the property and HOA fees for them living there?

I would recommend thinking through what your concerns may be and create a list of questions to ask each property management company you speak with.

I'm happy to invest in improvement, but concerned about fundamental issues with the buildings that may be more difficult to address. 

If I can't find better alternatives I can always swallow my concerns and live with it at least for the first 3-5 years.

I just started with buildium it’s ok so far but my big concern it’s all cloud based which is good and bad, do I own that data are only own it if I keep paying?