I've managed to save up a decent amount for a downpayment, but I'm feeling lost about where to even begin.

Cleveland is a great cash flow market, but you really need someone who knows the area to provide guidance.   

A bad PM can cost you a lot of money in the long run, and a good one can save/make you more than you would have saved using the cheaper option.

Another option is cash for keys but I have never done this but others on this forum have and can probably advise further.

I'd look into doing a cash-out refi on your rentals.

The higher rates have somewhat slowed down the "get rich quick with no money down" crowd as financing is more difficult, but I still see a lot of new investors with serious cash or purchasing power.

If you had 12 months of expenses saved up, would y'all go all-in with real estate investing/entrepreneurship path?

Interest rates are often a key concern for real estate investors, as mortgages are often the difference between a cash-flowing deal and a dud.

Maybe cash for keys on the one you’re planning to move into?

Best of luck to you, but congrats on saving $30-40K!