Nashville should certainly be there - regs (but well regulated, predictable) and is the favorite trip for pretty much all SEC Schools (best city by far in SEC, drivable distance, Vanderbilt sells out typically >2/3 of the stadium to opposing fans, etc.)

Well, okay a bit of an exaggeration, but they are distinctly different skill sets.The problem is you believe you've already achieved and I'm not sure you could tolerate someone else being the brain of the operation.

The only difficulty is I’m trying to find a multifamily property in an older housing stock area but nonetheless an owners unit inside a larger house is the goal but hopefully I can get lucky with the items you pointed out as well. 

Being 1.5hrs of NYC gives you a lot of options, even Long Island (which typically has more options for public commute into NYC).Give me a shout if you'd like to chat more, I have a handful of case studies on my site as well from deals I've closed/brokered that match the househacking criteria you're aiming for. 

We really believe in the power and efficiency of modular building for rental units as well as pursuing some seller finance deals.

I'm looking into this as well.

Those are great places to network and learn from seasoned investors as well. 

Presumably any potential buyer who refused to do this would not fare well in the bidding.

Rent is due Sept 1, it is odd for tenants to pay well in advance (unless they paid last month's rent with the deposit).4 weeks is enough to find a new place especially if they get started now and as they have one month's rent to use as a deposit for the new place.

I don't know Orange County too well to answer your questions, so will just add a few other tidbits as food for thought.