I know there's CAD programs and so forth but on smaller projects ($50-$60k in rehab) are REI people hiring interior designers? 

It's designed to protect you from sudden and accidental losses. 

I'm not a flipper, agent, designer, etc and not really up to speed on the latest and greatest. 

I would put even less weight if a 'financial advisor' is doing other services such as taxes / insurance because he / she is looking to make money in anyway possible.I personally think if you want some financial advice, you should seek someone with the CFP(certified Financial Planner) designation. 

We lived in the property for two years while we slowly renovated interior, landscaping, as well as resurfacing the pool, and added privacy with a new fence.

I have 40 years of experience in the home design and construction industry, a ton of skills, and talent.

In my local MLS, it may not be true in your area, there is a field that a listing agent can fill out to designate the home they are selling has a FHA, VA or USDA loan which by default would make it assumable.You can also reach out to your favorite local title company and ask if they can provide you with a search tool like TitlePro247 or provide you with a list of current on the market homes with a FHA, VA or USDA loan in place. 

I'm an interior designer and do kitchen and bath design.

I recently received a quote to paint the entire interior of my recently purchased home.

The success of an STR will depend on how it is managed, designed, and marketed.