And lastly, I search FunishedFinder listings nearby, find comparable properties, and track the listed rent for a few months (does it increase, decrease?).

The lender is the one who sets this up as they are the ones who typically pay since its them who is to provide this as well as keep track of the loan, but only be a borrower if they use a servicer.

But it's a start.While track record is very important, learning how to interpret a track record is just as important. 

It’s a lot to keep track of, especially when researching multiple markets.Would greatly appreciate any advice/insights from experienced investors who've navigated these challenges :- How do you approach understanding and evaluating short-term rental regulations when considering a new market?

These are all services that investors and homeowners will and do pay for so you're on the right track.

If you have a business entity(you want to properly track money going in / out from its owners).They will likely be classified as contributions / distributions.Best of luck!

You’ve got a sizable asset with stable tenants, but the monthly overhead is making it feel heavier than it should.

The track record of the guru and his claims of success have NOT been verified.  

But the answer for everyone may differ.Here are the personal attributes I see in those able to achieve a higher than market ROI, enough higher to be able to “scale”.1- Knowledge of real estate principles, real estate law and real estate finance2- Minimum 3 -5 years full time, or near full time experience directly related to real estate investing3- Ability to utilize technology for increased efficiency, capacity, and accuracy4- Excellent hired legal counsel and excellent hired marketing help5- Established method(s) of obtaining consistently high QUALITY deal flow6- Ability to manage and choose people who are NOT employees: Attorneys, Appraisers, Mortgage Brokers, Real Estate Brokers, Title Companies, Surveyors, Marketing Specialists, Accountants, Contractors, Consultants, Property Managers7- A VERIFIABLE track record of success8- Ability to identify, analyze, and negotiate a deal that can be “worked” for “enhanced” ROI9- Some type of competitive advantage; for example for me it’s my ability to analyze and identify mortgage loans that are actually less risky than all other lenders believe (on the investing in debt side), and on the real property side it’s my ability to analyze”pull the trigger” with LESS information than other investors need,  combined with the ability to pay cash, or raise significant capital almost instantly as well as being able to obtain loans at the lowest prime customer bank rate with no recourse or personal liability.  

Jonathan your on the right track describing Roofstock..