I would be cautious of considering it for less than a 10 year play.This is what we typically do (it is not rocket science):Purchase an RE that has a value add, ideally is a little below market value, in a nice enough area with good appreciation benchmarks. 

We have moved most things to technology - we are suiting up and offering 3D scanning homes for FSBOs, other brokers and our clients all free of charge.

Similar to your hard money lender, the hard money lenders I deal with have minimums that this property would not meet, either.

If it's your personal house, hard woods throughout would be ideal.

I know that landlord insurance is typically recommended with any rental property, but I'm not sure if its necessary for a live in rental like a house hack or if typical home insurance usually covers Should I get landlord insurance to protect myself or is a home insurance policy enough to protect myself from potential suites and such?

Ideally I'd like a 3-family (or 4-family if I can find one) that will cashflow with just 2/3 units occupied and me living in the 3rd.

That's the most ideal place to be for the season but that's it.

Search for what you are interested in here in the forums, read the answers, and start with the books that suit what you think you might want to do.

If someone gets hurt, your tenant likely knows who you are and their lawyer will name you in the suit. 

I plan to update the vacant unit that I will occupy, so ideally I would keep all of the tenants in place during that process.