She is very knowledgeable, thorough, insightful, well connected and just fun to work with.

Our first three years were fun and successful, this year has been a drain.  

You can imagine moving is not fun under those circumstances. 

Given this is your first investment endeavor, I would highly recommend going with an experienced and reputable management company that will mitigate your risk when the not-so-fun parts of property management arise.

You’ll have to chew through glass either way.

It turns out that when we ask about which cat scratched the upholstering or which dog chewed on the railing, it was always the other resident's pet.

I mean once you talk to them, it's pretty easy to spot if they know what they are talking about.I've work on STRs before and to be honest, it is not the most fun aspect of accounting because the volume of allocating income from all sources (airbnb, vrbo, stripe, direct booking, and so on) to a bunch of random expenses (cleaning, supplies, repairs, advertising, commissions, and all typical real estate expenses).I had to strictly rely on the client's input on what the expenses belong to which property or even units, if the paperwork doesn't say. 

I am a multifamily syndicator and having the right partners is crucial to the success of the deal and having fun while doing it. 

Everyone has already chimed in on the protection/ insurance side of LLC's, but one "fun" aspect of creating separate LLC's for each property is you can open up a credit card for each of those LLC's and easily keep all expenses on those property specific credit cards while racking up points and using those for travel and such :) This is a great forum thread and question!

With regards to the legal side of fun creation, that would be their parent company Fairway America.