Pueblo's housing cost on average compared to Colorado Springs is $150,000 less. 

Have you set up an email marketing list with something like Stayfi?

Is there any websites or platforms that I can add to my knowledge that help with this diligence at fair/free cost?

All the soft costs plus impact taxes. 

Carrying costs can add up quickly.

I will bring it up with my RE CPA!

I'm not exactly sure what you have in mind, but I know hosts keeping up with the current trends seem to have a plan in place for their seasonal STR.

Another agent mentioned that they may still look up the members of the LLC. 

I would calculate and compare the numbers of, first what the property might cost you to hold onto it versus selling and repurchase at a higher interest rate without a 1031 exchange.

As Chris and Justin note, the old adage of "vet the jockey (sponsor), not the horse" does not work anymore.While the sponsor can definitely screw up a deal, investing with the "best" sponsor is bad deals is a more surefire way to lose money.