I live near downtown, work as an agent, and collaborate often with investors.

That will help you prioritize those three markets or perhaps rule them out and look at others. 

Maybe we could collaborate somehow on early projects and learn! 

Residents can have a hard time prioritizing where the money should go.

I am also a new investor myself, we should collaborate some time.Ryan Boyce

A lot of your questions will be answered by yourself if you prioritize things and start tackling your action items one at a time.  

I don't have a degree, and in hindsight, I would be better off now if I had chosen to prioritize a decent paying job, with or without a degree, to help afford investing earlier/faster than my chosen fun but relatively low-paying field.

We'd be happy to collaborate with another local partner on any buy and hold multi-family deals or partnerships we find.

I would prioritize investing first and know the difference between an asset and a liability.

@Katie Greenman I would prioritize maxing out your Roth, and use any additional savings for real estate investing.