You may also want to consider any local regulations or restrictions on short term rentals, as these can vary by city and state.In addition to demand and regulations, it's important to carefully evaluate the financial viability of any potential investment.

Not so today, but not too far away either...The biggest differences:Conventional - typically a lower rate, no prepayment penalties, backed by the government or agency, DTI, Income, restrictions on property types, restrictions on # of properties owned, require passing AUS, can be difficult for Self-Employed, and heavy Underwriting guidelines.DSCR - higher rate (normally), prepayment penalties with various structures, backed by private investors or capital funds groups, about 1/3 of the paperwork, very laxed Underwriting guidelines, usually no restrictions on # of properties owned, no DTI calcs, no Income calcs, no massive amount of TRID disclosures, etc...Cost-wise (fees and such, not rate), they are very similar. 

I know each state is different and Oregon seems to be governed by a certain statute but I’m having a hard time figuring it out.

Often there are standard leases available online (from a government) you can use for your area.

This way, we continue to have cash flow coming in, and if we happen to have a bad contractor or one or two units and/or some permit/regulation related issues, the scale of the damage won't be too overwhelming. 

Do you think certain banks will allow it or this is all the government banks have no say so on it.

Now beginning to see municipalities regulate as in, requiring wholesalers to get licensed, I can't help but wonder what lines were crossed, who lost their life savings for that to happen.Think of real estate as an eco-cycle.

I think I would genuinely enjoy hiring contractors to fix up a home in a vision I see fit; and of course I would enjoy the profit off the sale of those flips.I have a decent job working as a government contractor in the IT field, but I have a dream to be able to leave that work and go all in with real estate someday. 

Many of these markets had vacation rentals long before airbnb so risk of regulation is low, and demand should continue to be strong as more Americans migrate to the south for employment and housing opportunity. 

Considering the massive amount of debt that Federal and State governments are in, I expect taxes to be much higher by the time I'm old enough to withdraw from these types of accounts without penalty.