Combine that with rates that are near high for this century.  3 things could solve this 1) RE prices fall (that would be bad for me) 2) rents increase a lot without RE prices increasing similarly (this would be bad for tenants) 3) rates fall a lot.  

I had similar concerns as a noob 16 years ago, what if I can't find a renter.

Leveraging PadSplit as an investment strategy now could yield profits on a similar scale to the windfalls earned by early adopters of AirBnb.I've been working with and investing on the PadSplit platform since 2017.

It's similar to an FHA loan, where you are buying it with the intention of living in it.

I see we have some similarities already, as I am located in Janesville, WI.

Agree with @John Morgan, we operate in a very similar way.

Could you advise where investors typically secure financing for similar land purchases?

It is so great to hear from someone with a similar start in one of the five boroughs too!

I’ve worked with investors in similar markets (Providence and neighboring areas) and have seen first-hand how house hacking can be a game-changer.. even in today’s fluctuating market.A friend of mine recently purchased a three-unit property in New Bedford, MA, just a stone’s throw from where you’re looking.

I have a similar situation where a Canadian investor friend and myself (a US citizen) are planning to partner up in Florida to flip properties.