Business owners won't want to get tied up in litigation and if there is a good chance they will lose, it is easier to simply follow the contract.How would that work with a lower-end tenant? 

My 2 cents: You're young, you could get a real estate or real estate adjacent 9-5 so you can get paid to to learn more about real estate while learning and building the side hustle outside of business hours.Seems like you live in a major US market so that's a plus, you could get a tenant services coordinator job in commercial real estate making $40-60k (not sure if that's more or less than what you are making now) It's an Entry level role, anyone with a degree and a polished resume and a passion for real estate should have a decent shot at landing a job like this.

Once it's rented, use that rental income to help offset your DTI, which may help you qualify for the second property sooner.Partner with Investors: Team up with someone to split costs and lower your personal DTI impact.

I can do that through charging points, but since I'm getting it at a lower rate than you could as a consumer, I prefer to mark up the rate while still being lower than most others in the market.

I know I already mentioned this, but @Mordy Chaimovitz...If you can get by with lower cash flow and invest for the long-term generational wealth (aka appreciation) in nice neighborhoods, that is the way to go, but it's tough to get by at times -- at least it is for me.Just know everyone's situation is different, and you should do what is best for your specific circumstances!

My concern with declining values, increased inventory and a weaker economy would lower rental income and could potentially put me into a negative cash flow situation.

Value add is the entry point of any property. 

If I can park the 388k ($415-27k) for one year at CD rate of 4.5% and then est 300k (after paying cap gain/depr recap) at 3.0% (assume CD rates lower) that interest income of about 24 months net of ordinary income tax is about the same as my current mortgage.Trying to play devil's advocate and think why selling this year does not make sense. 

Well that is when the lower tenant feels like paying her 20% portion of the rent of $240 per month lol!

The income amounts look to be long-term rental (which they are and came in 30% lower than what the STR average did) and 2. why did the appraiser look at homes 20 miles away to compare to when there are PLENTY of rentals in town...