I used to go to Beaver County ACRE back when I lived in Beaver County it was a pretty good group probably worth looking into. 

New Home: I would need to dump some of my brokerage accounts for the downpayment(so some capital gains taxes would need to be paid to finance the downpayment on the new house) or if I sold our "current residence(2nd home)" I wouldn't need to.I understand the tax incentive of selling within 5 years of living there for 2 years, however, the cash flow seems larger then what I would get taking the money and investing in new RE in the future. 

They know that with very little exception, it’s the primary use of the money that’s important, not who lives in the home.

All the Realtors that live there are driving Uber now or something.

You'll live in one unit and rent out the rest.

However, if you are starting out, especially with lived-in homes, it would be wise to have a home warranty.

He was just on our weekly masterclass, and has spoken at a couple of our live events.

Sure sounds good, I live towards you.

However, would I be obligated to provide housing (hotel) for the tenant due to being in a lease or do they just need to find somewhere else to live?

If you're willing to put your 10k into a deal and you have time to give, you could negotiate with someone who has some money and expertise to put a deal together.Otherwise, finding a way to utilize that 10k to a house hack, find some people to live with you and pay rent, gain some sweat equity, etc, and you'll be well on your way with your 2nd property!