You could even consider a condo with an established HOA that’s STR-friendly—it can simplify maintenance and management.A Few Other Things to Note: Documentation is everything.

Or should we just establish our LLC and get financing through a DSCR lender? 

This would be my first foray into real estate investing... and I absolutely 100% agree that the best move is to establish a track record using my own money and conventional loans before considering using private money.

@Wiley Hood to be honest, with all the new regulations around documentation for cost segregation that has come out, I recommend having a professional do them.

Make sure you thoroughly know how the regulators view the way things are being done, before committing to a "creative financing" technique.

I’d also focus on gentrifying areas, as their upside is usually greater than established hoods when the market cycles up again.

Hoboken has stricter renting regulations than Jersey City.

Ensure that you check your state's regulations and requirements regarding security deposits.

Best bet is to carefully analyze the zoning maps and regulations or just call the town and ask.

Issues with multiple national carriers leaving the state completely due to state regulations, massive loss ratios, huge increases in replacement cost values/limits due to inflation, etc.