No STRs according to the HOA. looking at this from an investor/family man lens what pitfalls am I missing?

I do have a team here to help me, not a one man show - time just would not allow for that - but anytime a client, potential client, or just another investor like myself has any concerns are questions I am here to help and would certainly do my best to get back with you. 

I have an MBA and I work in Corporate Real Estate.

My maintenance man tells me it's infinitely easier to install.

If asking me I'd say that is "The Richest Man in Babylon".

But still trying to conceptualize how to incorporate ongoing expenses/interest payments and loan paydown into that equation to get a more holisitic image before deciding where to live

I also like the idea of  having a "scary man" who appears to be incharge so I can just look like I am a helper, instead of incharge. 

The company is a 1 man guy who subbed some of the work out to a big environmental company, unsure of what exactly.

I'm with you man.

Perhaps some of these amenities come later (schools, retail/commercial) but selecting markets that have the capabilities of incorporating these features is a good start.