The roof looks in relatively good shape (I don't know the age) although I did notice a very small leak in one part of it and the facia is rotted in several places. 

You will burn through several of each before you settle on a more permanent person, and even then they can disappoint at any time.2.

I have done several as you explained.

I am personally working through a few BRRRs and have several clients in the same boat.

I personally never would, but I would talk to people that have that can give you an idea of what it's actually like instead of getting opinions from everyone who never have and say it's the worst.Jacksonville, FL has been great from 2010-2022, but there has been a huge surge in building residential from 2020-2023, which severely impacted the supply and demand balance and rents have flattened or dropped from 2022-today.

You will barely notice when things are going well for several months, but when things then go poorly you will be able to think about nothing else!

I am part of several Facebook pages with Agents Invest (Jennifer Beadles), Bigger Pockets Money (Scott Trench and Mindy Jensen), and Afford Anything (Paula Pant) communities and I have never paid a single penny for a course.

My family in Texas has several real estate portfolios and their taxes have increased over 125% across the board in the past three years.

There are several smaller satellite events each month as well. 

I've worked for several PM firms in the area and one company stole like 30k in commissions from me when I no longer wanted to work at their god awful company.I can definitely advise you on some property management companies to stay away from, as well as some new and upcoming property management companies in the area that are taking a more hands on and professional approach.