If you're hitting up Cleveland I'd start by reading The Ultimate Guide to Grading Cleveland Neighborhoods. 

Once you hit maybe around 20 apartments units plus, then renting them would potentially make more sense in my opinion. 

We are looking to leave the state but will be hit  by capital gains. 

@Mario Morales I'll add that if you choose to work as an Owner/Builder and don't follow all the laws that a GC does.....you can/will be hit with penalties/fines/jail time.

There is always a risk of getting hit with a special assessment however.

I'd like to see your success stories from those types of approaches, I'm just a guy getting hit by 10 of those a day.

I know I’m going to take a hit to cash flow with the refi, but I’m okay with that.The other conundrum I have is, if I have all of this on paper/in writing to show them the numbers all add up, how willing would a bank be to loan me the remaining money?

As a bonus, once my stocks hit a certain level and I find a new investment, I can take those out and use it as a down payment for a property.

Yesterday, I got "good news, we removed our extra 2nd home / rental property hits, because we're so generous and nice!" 

I want to be able to hit the ground running when I turn 18.