I am not a realtor, so I cannot give advice as though I am one, but there are some guidelines that I have used personally over the years, with great success.

Referrals from local investors on BiggerPockets can be a great resource. https://www.biggerpockets.com/business/finder/agents@Mark Ainley sounds like a great person to link up with!

I personally don't like getting a lot of automated messages when I rent a STR, I'd rather have some more personal contact.....

Unrelated persons ordinances are common. 

Look, I have no idea who Eric is, what type of person he is but I will say after a quick search I saw that he did in fact sell his company for MAJOR $$$ and that he is active in Section 8, no idea if his course is good or garbage but still felt the urge to respond because I am so tired of hearing SCAMMER, find it online to EVERY SINGLE post asking about any course. anyone who actually sells their business and nets 110 mil is NOT going to dive into Section 8 or any real estate for that matter other than fine personal residences etc.. they retire and spend it.. so I dont think so.Plus section 8 is simply not complicated its run by the Sec 8 folks in each city.. nothing magical about that.. its a tough way to go being a section 8 landlord lots of drama.

Take a look at Personal Property versus Real property coverage, plus clean up costs to make sure your covered.I would also look at covering your project from the Subcontractors. 

And you can't legally dictate how much they carry for personal belongings. 

I would still use quickbooks to track the finances in that account snd all rental associated finances (we use it to track are personal finances also). by the way it is worth the cost of paying someone good with quickbooks to do the initial setup.  

Out of all the tools I would personally suggest Pricelabs for sure.

Each week, I personally analyze the MLS, leveraging my deep knowledge of South Florida’s short-term rental market.