You will likely run into a lot of late-20's/early 30s guys doing this, who have a lot of confidence but not a lot of experience.Overall, I think the biggest thing is finding a group that generally has the same outlook as you. 

I'm not sure I have full confidence in this property management company.

There is real estate to buy 24/7/365 when you have built the confidence to do so.

Who else do I need to confidently manage remotely?

My RTR strategist confirmed multiple times their very high degree of confidence in the RTR monthly rent projection, sub 30-day vacancy rate, and PM team performance.

I currently own a successful short-term rental in Fort Lauderdale and have identified a new property nearby that I’m confident will perform well.

My agent was a very nice older lady, but no idea about investing, it all worked out and once the first rent checks started coming in started gaining some confidence.

@Hunter Duplantis what @Gino Barbaro said is exactly what I was going to suggest.When you have vacancy is the time to experiment and apply your original thesis.I’m not trying to play Monday quarterback here but, you should be highly confident in where the rents should be well in advance of having a vacancy.That being said, after confirming competition rents on websites (I’d also recommend Craigslist and Facebook marketplace), you should be in alignment there.  

I'm confident a judge would see the picture evidence I have and go "damn!"

I picked up the BRRRR method book and feeling confident in setting it all up (we did a similar process for our Airbnbs).