Looking at getting a STL in Snowshoe WV, first time

[Adam Smith]

Hello everyone, I've never owned any property before and I've been looking at getting a STL at Snowshoe WV. I have lots of questions and would love any input.

My goal is to get a place I can use quite a bit, but hopefully rent out to cover at least any mortgage and operating costs. This being my first venture into real estate the lower risk/stress/trouble the better.
I have about $60k in cash, plus another $40k I could access but would rather not. I have no debt, and have been living very frugally since the pandemic hit,

At a glance Snowshoe seems like a great opportunity. My friends and I could use it year round for Skiing as well as mountain biking/hiking/nature exploration. The cost *is* historically very high like the rest of the market, but not prohibitively so. 1 Bed condos go for ~90k - 150k and 3 bed go for $250k - $350k. The HOA rates for the area are very high though with a 1bd being ~$400 and a 3bd going up from $600-800 / month.
I've seen a lot of mixed reviews on this area from "Its very hard to break even due to the high costs and special assessments" to "I bought a place here for 50k 3 years ago and am making a killing" so I'm trying to find out if it is actually worth it.

I did get an AirDNA subscription for the area, but in all honesty it is very difficult to derive much insight from it.
The big questions:

1. 1. Should I even be looking now? The hot winter rental season is only a few months away, I would love to have a place before then, but would I be paying a premium pre-skiing season? I do believe that the market is going to cool off quite a bit in the coming months, this is my personal thought granted it may not be true.
2. 2. 1 Bed vs 3 Bed; I could easily afford a 1 bed condo and purchase any furnishings. I could also support it as a pure cost if worst case scenario there's another covid shutdown or we head for an apocalyptic great recession. I would really like to get at least a 2bd if not a 3bd 2ba so I can have groups of friends join. It does increase the rental price, but according to AirDNA the occupancy rate seems to be about the same, and if there's an increase in utilities/management fees etc it almost looks like they would bring in the same amount after costs.

Other questions:

1. 1. Does having a condo in a building with more amenities like a hot tub draw more renters, or is it mostly based off of price and how many people it can sleep.
2. 2. Is there anyway to see historical "Special Assessment" charges for a condo? I've heard these happen frequently and can be pricey.
3. 3. What could I expect for typical utilities charge?
4. 4. Ballpark how much does it cost to furnish a rental, specifically 1bed vs 3 bed.
5. 5. Property maintenance rate?
   1. Typical cleaning costs? Is it directly attributed to the number of stays?
6. 6. How are owner/resort relations?
   1. I've seen some subtle hints that the resort is strict or controlling in some way?