I wanted it for a rental and knew that the size of this huge thing would be difficult for a tenant to rent and heat through the winter.  

-Charlotte is one of the top 20 fastest growing cities in the country-The weather is amazing we have all four season and mild winters-Strong financial industry where many of the big banks have their headquarters.

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.

., or people with boats and jet ski's that need stored in the winter.

The mold must be terrible and I expect that the furnace is completely rusted out.There's about two inches of moss on the roof and the porch.Considering that they are going to need to pay 5k in property taxes, get a quiet title, pay a REO realtor, and get the place up to code for showings or winterize, is it possible that they won't show up?

I’m thankful we’re having a light snow winter with relatively mild temperatures because he’s working on renovating 6 units simultaneously for me!

Seems to me you should have no problem covering expenses in winter.

In particular, I've seen potential for this to happen in Grand County (Winter Park & Fraser) + Mount Crested Butte.

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!

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.