I love it here, but want to have a place of my own to rent out for income, and go visit whenever I want.I have stayed at some resorts that have a condo/apartment section that you can purchase, and the resort takes care of marketing, booking, cleaning, etc.

None of my refi appraisers have cared about a new furnace or windows or roof, as long as whats there is functional.   

Since you're in Akron, be very careful of the area you are purchasing the 4-plex in.

Question 1: Even though we are careful to track ALL rental expenses that are paid using our personal credit cards, is that enough separation from personal accounts or MUST we open a separate credit card for each LLC? 

These tenants usually have a decent credit score and care about keeping it that way.

Kris thanks for the tips.

we have our savings parked in a high-interest one as well, but that's an outstanding rate.flips "scare" me - but anything that scares me is something i'm willing to try. i find it intimidating to find a flip team. i'd rather not do any/much of the work ourselves - that wouldn't be passive income. any tips?

That's a great tip, expect a minimal 90 days grace period to receive funds from borrower.

Buy within your comfort level, but always know no one is going to care as much about your investment as you do, so make sure you are mitigating the risk of OOS as much as possible.

But sometimes, it takes careful selection and interviews to get the right person.