I have had some really bad interactions with James Wise over the years, but I always have pointed out that he is a reputable agent and he has built a good business.

While I like the idea of locals with local intuition, I preferred the approach of the last one from Century 21 who explicitly stated his goal is to minimize my costs to bring it to marketable condition.

I think this can sometimes run counter to an STR owners intuition.

Intuitive and easy to use once you familiarize yourself with it (which didn't take much time).

Probably because most guests prefer that personal interaction.

How comfortable are you being a landlord and interacting with tenants daily/weekly?

Honestly, if you only have 1 property, you should probably manage it without the software for a few months so you know what is supposed to happen, how the interactions take place and then decide if you really want to add a platform manager to it.  

This is all based on my subjective experience and intuition, but the biggest questions I asked myself in deciding how wise it was to take on more debt when I already have debt were: 1).

As I've experienced, the more people who see and interact with your brand, the more likely they are to reach out and express interest in investing.Nurturing relationships with investors through ongoing communication is vital.

Again, the BiggerPockets store has some books for this or you can learn by watching podcasts, reading blogs, and interacting on the forum.