Was curious if having a multi-family I could live in and house-hack as a starting point is actually a smart idea or just one that's going to set me back financially?

If you can find a MB who will allow you to keep contracts when you jump and mentor you, that's a good deal.

With recent changes in the market, I know there a lot of smart investors in the Dayton area who pursue this strategy and have swept in to pick many of these properties up.

You’ve come to the right place to connect with some very smart investors.

Perhaps smartly convert it over to a Roth IRA to have tax free for the rest of your life.  

Either do the blocking and tackling of one on one help here or stop with the "I'm so smart, you should be better" nonsense. 

Smart - I would have never thought of that!

You’re setting yourself up for long-term financial growth, and teaming up with your friends is a smart way to ease into it while covering your mortgage.A few tips to keep in mind:Location is key.

Quote from @Diane Forgy: I have a commercial building under contract and am now considering investing my proceeds into DST's.

Most states require you to be licensed to perform a wholesale deal in which you negotiate a contract, market that property and contract and then assign it for a fee.