For the rest, just a bit of current experience will get you comfortable knowing and 'feeling' the market.

I’m sure your ID will know that but you want warm and comfortable not just ‘my’ style.

I personally wouldn't feel comfortable renting to someone whose only source of income comes from UBER, especially if it has not been that long (under two years).

You would also need to know the true purpose of the operator and have it spelled out in the contract in the event they pivot to something that isnt allowed per your HOA or something you aren't comfortable with down the road.

Yea, I wasn't intending to manage for others this year but it fell in my lap as a friend's fiancee has her old place she wants to rent out... so I thought I could help a friend out when they asked and get outside my comfort zone and grow a little.

Mathematically, it makes sense (I think) to maximize our loan, both in terms of duration and amount, on the personal property and use that money for investing.

Needs a lot of work, and would like to maximize the square footage. 

If I lived in one of the neighboring Toledo suburbs (some beautiful houses there, BTW), I'm pretty sure I'd be FI and living comfortably right now as I agree with @Russell Brazil.. the best market to invest is the one you are in. 

Your ultimate goal should be to maximize your income and have staggered expiration dates, which will minimize the risk of having multiple vacancies at the same time.  

I need to save up a reserve fund first, as I don't have a comfortable amount (I want about 10-15k) yet.