I’m guessing the ski community is highly seasonal and has deep-rooted family traditions of return vacationers.

I am also following your opinion and analysis as well.You were said before that you met this hedge fund guy (or whatever) that their AUM is hundred times more than your AUM correct, but while you able to manage your portfolio and management, their portfolio is all at red. 

Major red flag for me that they won't give you one.

So be careful and make sure you interview the Expediter and that they have had success in obtaining the Letter of No Objection.As far as evidence that you need to gather, look up your buildings TAX Class.You will find it here: Building Information SearchHere you will see something that looks like this:NOTE that while this is a Dept of Buildings Web Portal, what I have circled in RED is the Department of FINANCE Building Classification.You may not have a CofO, but the Dept of Finance maybe taxing you as a 2 Family.

Hopefully, some others see this.Yeah, I would say that's a red flag about the LLCs because usually when an LLC buys and flips, they sell to an end buyer/homeowner, not another LLC.

It is seen as a red flag by a portion of the parents.

I got lucky that the tenant wanted a house in my neighborhood to keep kids close to their schoolsHouse was listed for 1750, they offered 2250 but I declined , so they offered $3k, ended up renting the house for $3250 ($250 pet rent) per month, for 3 month, open to extension if needed.I met the tenant and did the background check on them, I felt comfortable renting to them THD takes time with approving the property, but they were quick to approve the lease, and they sent me the checks the next day after lease signingMy house is not furnished, and they were ok with that , they actually work with a company that provides furniture for the tenant, and they coordinate the delivery and setup of furniture on the lease start dateOverall I like the experience working with them , but hey today is day #1 (out of a possible 3 months), so I will update this post if anything wrong happens or if I notice any red flags

I know Red Awning charges 10% and they handle most of the guest communications and listing, pricing for you, but you still need to arrange cleaners. 

DSCR loans offer more flexibility with long-term fixed rates and less red tape.

Do your research on the forums for general tips on hiring a PM, what to look for, what to look out for, good stories, bad stories, learn from others about their experiences with all kinds of PMs all over the place and take what you learn when you're speaking to PMs in your area so you can more easily see red flags, or green flags!