Wondering if we should learn the bumps in the road now and try to self manage with some recommended tools or to put our property in the hands of a Vacasa/Evolve/Awning type company or maybe a professional local outfit?

One thing to keep in mind is that you can't use an FHA loan for an STR, so you'd have to go conventional or another loan type. 

Unless someone is very comfortable with all the rules regarding SDIRAs and prohibited transactions, we don't recommend these types of entities.We have never had any complaints from our clients who hold real estate directly that there are too many delays or too many fees.

After some basic research, it seems to me that an FHA loan or, potentially some type of physicians loan may be the best option.

In continuance, what type of returns are outside investors looking for typically?  

I'm also wondering if you have space for an ADU for your current house, as this is a popular trend in Seattle.

It allows you to include the land into the financing with the build.It is becoming very popular in multiple states to find a nice piece of land or land lot and put a "Modular" or Manufactured home on the land.

It's actually funny....I heard the news break about the 'good economy' while listening to a show on Sirius POTUS channel with a national expert throwing out depressing numbers about the huge numbers of people living paycheck-to-paycheck (40-something %), and the increasing popularity of using these Payday Loan places (12-something %)So no the economy is not doing that well, but they can cook the books to make it look good (and both sides do)....

as far as having a lender in the state you want to buy in, i don't personally think that matters, as long as you know right away whether or not they can lend in that state (many investor-popular lenders that i've talked to can't lend in MA, which is where i live). 

What type of real estate investments are you interested in?