Thanks for sharing your feedback on Stessa as I feel that not having a good response time from any entity is an issue for most automated systems with no strong back office support.  

With the new spam regulations coming in, I’m feeling like cold calling might be a thing of the past.

Any advice on how to get out of this stagnant stuck feeling?

In addition to what was said above, for the software that has a free trial option, sign up for it and use the software for a day (or at least a few hours) as if you are using it for real, then call their customer support too and get a feel for that. 

Just about everywhere in the US uses some version of IRC for its base code and then makes some changes to that as they feel necessary for their locality.

Quote from @Shiloh Lundahl: @Jay Hinrichs so it sounds like you don't feel like you got punched in the face by real estate over the past couple of years. 

In fact, it's a common and expected practice.What rule do you feel was violated?

I feel both offer a tremendous amount of value.

WordPress, especially when paired with plugins like WP Rentals or a property management system, offers more flexibility for custom features like dynamic calendars, booking systems, and integrations with platforms like Airbnb.If you're planning to grow beyond a few properties, WordPress can handle that expansion better since you can continuously customize it as your business needs change.

You've likely used tons of different CRMs coming from sales, and HubSpot looks and feels the part.