@Thomas BaylorI think it'd help to work backwards and then start determining which areas of town support your ultimate goal. 

In this case, working with other owners to change the neighborhood will be difficult and incredibly challenging but will ultimately provide a fantastic opportunity Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I made a handful of folks a lot of money, learned the ins and outs of transactions and how to responsibly get creative, and I learned what space I ultimately wanted to be in and where my strengths lie.

So yes, it’s important to note but ultimately it is only an indicator of future cash flow.

My ultimate goal is to own something near a beach.

He ultimately wants to maintain & manage our rental (and any future rentals) but will initially have large gaps in his schedule to fill with paying work once we arrive.

In other words, if I get one person's rent but not the other's the rent is still late, and can ultimately lead to an eviction for BOTH parties. 

Be sure to read through The Ultimate Beginner's Guide to Real Estate Investing to help you get started.Check out the BiggerPockets #AskBP Podcast too. 

We did become a little jaded after that but ultimately got around to some critical introspection, owned our mistakes and learned some lessons.I’m in my mid 40s and am focusing most of my attention and energy learning about multifamily residential and small apartment investing.

Am also a newbie working on my real estate goals .Make sure you download and study " the ultimate beginners guide" .