To preserve the Tax Advantage of selling a personal residents (Section 1031 does NOT apply), you need to occupy for 2 of the last 5 years. 

Before making any decisions, I recommend exploring neighborhoods in person, talking to locals, and doing thorough research to determine which area aligns best with your preferences and lifestyle.

@Nick Rutkowski I have not personally but know people who have land contracts and lease the land to large corporations to build to suit.

|As far as an inspection goes, Michael Bender is the most thorough inspector I've ever worked with and the only one I would use on my personal home.

It depends on what demographic you are aiming to serve.2) BiggerPockets, Facebook, in-person meetups.

I personally like to buy real estate that has A) excellent long-term prospects ie. area growth, commercial vibrancy, high housing demand, rising rental rates and B) positive or at least neutral cash flow.

Seems like your brother would be the person to ask.

I personally hate this because incentives are not aligned.If things go wrong with the property it's the PM's fault.

I don't know the guy personally.

As far as you saying you don't know if it's in an HOA, it likely is, given how you described it and that shouldn't be hard for you to figure out just by looking at a Google Earth map (sometimes the name of the community will appear), or pay a local person off Craigslist to go drive it and find out the community name, take pictures of the lot, etc.