My approach is somewhat unique since I'm a builder; I build my units from the ground up and then decide whether to use them for LTRs, STRs, or sell them outright.

Don't be held up by analysis paralysis.

You would then use a hard money lender or another private lender to purchase a property, including repair costs.

Hey Mitch, new flip opportunities are coming up every week here in Ohio!

Cleveland is a big place and not every area can do OK with a STR.Go hit up Airbnb and VRBO and search on the area right around your place.

Start attending local meet ups.

He has a good job but no savings built up. 

But if you already own the home, if you have a skill set that compliments theirs or the downpayment money, their experience may be leveraged to finance the deal.And there is always the "friends and family" approach of trying to get one of your relatives to put up the money, either as a loan or equity, to get started.  

I think we can all agree millennials who live with their parents to save up for their financial future is a great idea.

Go to local meet ups, join local facebook groups, talk to realtors, etc.