I am looking to live here and eventually house hack so as this opportunity already has 2 trailers it seems like a great fit for me. 

No signing expensive leases that you personally guarantee typically. 

You have to drug test and these are expensive.

They don't expect you to live there for half a year, but it is more of having the ability to. 

I also closed on my first house hack a couple months ago and had to get a tenant out of the space that I was going to be living in.

We will renovate the fix up the first floor additional dwelling and plan to rent it out as a STR for the rest of 1st year to maximize the return of our renovation expense against our W2 taxes via the Cost Seg / Bonus Depreciation.

I'll make it expensive so it seems valuable if that helps.

If he's that good of a contractor, why is he so desperate to live in your basement?

The contractor has to live in the Bay Area, so their cost of living is just as high as the client's.I was daydreaming about dropshipping contractors into CA.

I started real estate investing, while living in New York City and working as a leasing agent in my early twenties.