It's the best way to test what you like and don't like in a low risk environment.Once you've done this, you'll probably have even more saved up and experience to make you more confident in choosing a direction.If you decide to just dive into one of these markets and strategies, I'd recommend focusing on your personality, goals (cash flow first or something else) and how much time you have.

If I die of natural causes...even spouse can't use it. 

I have tried to bring up those expenses in a few of our conversation, and even though they are aware of those expense since they also investing themselves, they still don't include those in their analyst. 

Creating a holding company, LLC, business cards, websites, and all this other nonsense is like buying an indoor basketball court so you can pursue your dream of playing in the NBA . . . before you even try a pickup game to see if you are any good or like the sport.Buy an investment property and learn how to manage it.

Even if it wasn’t another window, something in that void would really help.

Because I had everything in place, it wasn't that bad, but even now, I always use property managers for my out of state properties (and a couple local one's as well).Second, You just need to search around for a property manager that meets your needs.

Make friends in the field, be patient, keep going even when it's hard, and be ready to change when needed.

When I say good I guess my parameters would be the usual items like protection, anonymity (if that's even a thing) etc...Thank you in advance!

Is there anything I need to know, is this even possible, more importantly would it even be worth it??

The mortgage payment on this house was roughly $1800/month so when we get tenants (or technically roommates while we're still living in the house) we figure we would have them split the rent evenly, or as a percentage of the house since someone could have the entire basement to themselves.