We have one property already as our primary home with a plan to buy another house and rent out this one.

In my home market of Florida, our insurance rates have made it much harder to have positive cash flow on a CRE deal.

If you don't own a primary residence I'd start there.

I guess I could do some work-arounds -- maybe reserve one unit in the first purchase for use as an AirBnb, and reserve my own time in it when needed - instead of claiming it as a primary.Are either of you (or anyone) familiar with a finance product/loan that will allow me to purchase under $150,000 (w/ strong credit) and do much of my own work and live-in a portion as a primary residence?  

I’m starting off wanting to get into a primary residence that I plan to house hack and then figure out the next move into investment properties but that’s down the roadwith all that said, are there other ways that im not thinking of to 1.

I have the funds available today for the purchase of a rental property as well as a primary residence, but I also want to set myself and my wife up to reach financial freedom.  

My primary focus is on the BRRR method, with a greater emphasis on appreciation over cash flow.For those with experience investing in Cleveland, I’d greatly appreciate any insights on neighborhoods worth focusing on.

This defers capital gains and depreciation recapture taxes on the sale of your fourplex.After converting it into your primary residence, you may qualify for the primary residence capital gains exclusion ($250K single/$500K married), but only for appreciation after the conversion; gains from the rental period remain taxable.

Or turning your current residence into a rental and buying another primary and living in it until you can rent it to cash flow. 

I would love to benefit from the savings of grouping the listings as a primary with add-ons, but the last time I tried that, there were multiple issues on their end.