Another consideration is that if you do a 1031 exchange back out of CA the state is a "claw-back" state so CA will try to get their capital gains eventually.

Not every lot will allow you to STR even though sevier county and the city propers do have specific zoning that allows it so you don't have to worry about them ever rescinding that right. 

Expect to spend a considerable amount of your time speaking to people.Expect to work dozens of hours/week with little to no immediate result.Expect most of your early interest from potential clients to come from your sphere of influence.Expect to go 3-6 months without getting paid (unless you do rentals which usually pay faster)Expect to be bombarded with distractions - mainly, people/companies marketing to you so that you choose their system for quick and easy buyer or seller leads.

Initially, tell him the considerations with the options and later ask him what he thinks of the options, then explain the considerations.

Instead of this, I find it more helpful to look at percentile performance across the market for a specific asset type, and also to check comps.

He had specifically said he’s okay with the north fencing and knows its to keep the homeless campers out, and who the police are very slow to remove.

Specifically, I’m drawn to distressed properties, such as pre-foreclosures and foreclosures, because of their potential for strong returns and lower acquisition costs which I feel is a great combination for a new investor with my budget.That said, entering the U.S. market as a Canadian comes with its own set of challenges, and I want to make sure I’m approaching this the right way.

I would also ask about your area specifically about how it is covered.

Raising rent by a specific percentage isn't a very accurate way of handling this.

No, more specifically deals found through networking with local real estate professionals, finding pocket listings, direct mail, etc.