Personally I don’t have enough assets yet to be too worried about financial liability and have structured myself to be covered with the insurance on my properties and a very solid umbrella policy, an additional $2 million.

Pick a solid B-Class suburban area.

You'll gain acquisition experience, project management experience and property management experience which will give you a solid foundation on which to build your portfolio moving forward.Best of luck to you moving forward!

But when your brother at the same time moves from a $250K single-family in a solid neighborhood to a $750K McMansion in a new development, and you haven't bought a car in five years, well, if you explain nothing, your brother is going to automatically assume you're going broke.

Thanks @Ramesh Ramabhadran this is a solid list.

Its a great way to build a solid foundation personally and professionally, and the benefits are substantial (GI bill, VA loan to name a couple). 

The time investment is learning compositing, your editing package, and lighting.Nobody can edit a crappy shot and turn it into solid gold.

You can get solid place but it's incredibly far from everything Tampa has to offer thus, lowering the amount of people who could potentially be interested. 

My credit score is solid though.Is there anything that I am able to do >presently< to work my way into a 4 flat, house hacking situation or do I need to get some things done first before that is possible?

Home would be located in Florida, for anyone who may be able to connect me to a solid lender that has experience with these and can walk me through all the options.