If you end up in Cleveland you'll want to read The Ultimate Guide to Grading Cleveland Neighborhoods to give yourself an in depth idea of the market.

But it gives an idea of the basic considerations and protections you want to have. 

Your idea to begin with wholesaling and then expand into rental properties is exciting! 

I like both of your ideas so I would look for the single where an ADU is permitted or one with a dump ADU to renovate (that's best) and balance that against the purchase of a 2-4 unit.

I feel I have a rough idea, which is..I'm in Rogers Park, my next important step is to wait out 1.5 years until I can fully rent out the condo, but for the meanwhile get a roommate to save more money.

Also, the idea separating them is so you don't accidentally spend them and then no way to pay it back when the time comes.Some states if you don't refund the security deposit within X amount of days, the penality is that you will have to pay back the security deposit x2. 

My story, with 1/1000th his wealth (or less.) builds on Jay’s idea of zero debt (I only have a dozen homes worth mid to high 7 figures, but I owe zero.), along with his idea of where you come from and your life experience determines what you need to feel like you couldn’t spend all your money without wasting it.

Ensure you understand local regulations regarding permits; it’s usually a good idea for your associates to form an LLC for liability protection, but individuals can do renovations as long as they pull the necessary permits.

I currently am working on a project and have a ppm my lawyer is finalizing a few things on and have a few ideas on how to raise but wanted to reach out to hear from other investors that do have more experience in this area. 

@Joseph Gary It's definitely a great idea to find properties with little to no work especially if this is your first time doing out of state investing.