Househacked and renovated myself, allowing me and my fiance to live for cheaper than we were renting.

The drivable option will be less expensive and make your life better. 

I have extensive background in construction and real estateI lived in Florida and wholesaled & syndicated real estate for a few years.

My name Sean and I live in NJ.

However, multi-family deals seem to be expensive, overdeveloped and in short supply on the MLS. 

If you can find one it's pretty expensive. 

Some places will be little cheaper some more expensive

Homes have been getting more expensive and I want to see if it’s possible to get a second heloc on my primary residence.

Quote from @Dan Hinz: My business partner and I are looking at buying a property in Akron, OH, but we aren't intimately familiar with the city yet (we both live in Florida).Other than virtually driving around on Google Maps Street View, does anyone have any suggestions on how to analyze specific areas and neighborhoods?

I've lived in my primary residence in Reynoldsburg, OH since 2015, house is almost paid off (just a few grand left).