.- If purchasing and/or improving a property, consult with your CPA on how to mitigate taxable events (for example, if you have to sell stock you own to fund the investment).There are many other questions that could be asked, but given that I do not know much about your situation, I am not sure if they would be relevant.

You get to share expenses...When you need a major improvement (like a roof or parking lot) you get to split the cost with like a hundred neighbors.

There are other advantages to owning 5+ unit versus a 3 or 4 unit building.  

They have improved some lately, but I am pretty sure that is because I started really letting them know I was dissatisfied. 

As someone working with my father's home improvement business for the past 11 years, I have worked on multiple flips deals, just not on the investing side.

So if I was in your shoes, I would put a little work into the curb appeal to improve that first look. 

Tell him your concerns, see where the breakdown in communication is, and figure out how to improve it going forward.

Anyway, the HOA is saying that not only do I need the typical exterior paint color approval and any sort of window shutter approval, etc, but there are HOA "fees" associated with improving one's property.

I enjoyed reading the details of your business plan and enthused to improve my own and add more detail.

The additional fees associated with incorporating/forming versus the hassle of having your LLC registered is way much easier, so we are talking about few hundred vs time+risk.