As for valuation, I see no reasons why a Junior ADU would negatively impact additional housing unit.

Jefferson County, which technically allows short-term rentals, is fickle with permits and just revoked one of my clients' permits for arbitrary reasons.-- The biggest indicator of turning public sentiment was just last month, in December, when voters in Woodland Park approved a ban on vacation rentals that also appears to NOT grandfather in existing licensed properties. 

Negative cash flow combined with historically slightly poor appreciation would lead ne to exit unless I had some reason to have confidence of appreciation above its historic rate.https://www.neighborhoodscout.com/ok/yukon/real-estategood luck

Since we are in FL it could be citrus, or some other local good we can get at a reasonable place. 

Over the last 10-12 years, the city’s been on a steady climb, and for good reason.

Instead I want to take advantage of the opportunity I have of living rent free to invest my time and money in STR's to hopefully build that portfolio up and eventually make that my main source of income (I understand that will take time).

I actually just finished reading his book and was surprisingly disappointed for a couple reasons.

When evaluating a property management company, it's important to look beyond just the management fee and consider the full scope of services and costs involved.For example, at our company, we charge a 10% monthly management fee, a $250 lease renewal fee (unless it’s a takeover tenant, which requires additional effort to establish a strong relationship - because usually people are changing pm companies for a reason), and the first month’s rent as a leasing fee.

My main question is whether it makes more sense to go the seller financing route and pay off the principal in 8–10 years or stick with a standard 30-year loan.My thinking is that the tax deductions from a mortgage wouldn’t outweigh the potential equity I could gain over those 8–10 years.

no reason to go out of state when you have the metros you mentioned close by.