It’s not a binary on/off choice.

For someone new to real estate investing that wants to do long term rentals, do you recommend starting off in an area close to them/an area they're familiar with or someplace that will give them the best return even if it's out of state. 2.

If that's a turn-off for you, then don't go.

I started off wholesaling and I closed on 7 properties.

Had a quick question.I purchased the property for $500K about 10 years agoI'm selling the property for $575K with the Fire DamageI received an insurance check of $380K for the fire damage.After Paying off the Mortgage + Escrow + Realtor Fee's, I'll be left with about $150K.My question is will I get taxed on this $150K?

You're better off self managing or going with a local company with boots on the ground.

I think your starting point is off - way off. 

If I were ever forced to take Section 8, I would start selling off anything I had in that jurisdiction.

If indeed it is stated that the second lien foreclosure is subject to the first, then no, the first will NOT be paid off. 

You’re not going to find a safe way to do what you want unless you or the “buyer” has enough cash to pay off the note.