I'm hoping to be a hands-off STR owner so was interested in Evolve and/or RedAwning's services to manage bookings and optimizing my property's listings on multiple booking sites such as AirBnB, VRBO, Booking.com, etc. 

I will mention in a later post on what your landing page and thank you page should have, for now just do some researching on google.Optimize, optimize, optimize...

If we wanted to optimize our lives for a low cost of living/tax burden the most opportunity for building our real estate portfolio in a beginner-friendly market, where should we be looking?  

When it comes to investing, the tasks that I consider to be worth more than $400/hour include things like finding deals, negotiating, scaling/optimizing my business, networking, and handling some of the legal/protection aspects.

I agree that Chase is probably not the optimal lender for this situation.

What does, "significant upside potential through optimizing operations" really trying to say

It’s hard enough to comp STRs bc less-than-optimized pricing can suppress total revenue significantly even if the property & mgmt are otherwise comparable to what you feel you can deliver. 

You get larger companies doing a lot of Search Engine Optimization in local markets and larger companies paying lots of money for Ads.

Suggest you take a look at their keywords to help them optimize their site.

Made sure water heaters were operating optimally and replaced those that needed it.