Waterbury, VT Advice Condo vs. Multi-family

[Kayla Flynn]

I am currently looking at condo's and multi-families near Waterbury, VT. First off, I am hoping to initially live in the condo/multi-family 5x/week for 2 years, and then 3x per week after that. So, I was drawn to condo's for 4 reasons:
1. There are plenty of them, because this a ski region (sugarbush/stowe).
2. They are cheaper (in terms of sale price)
3. I could rent them out on Airbnb when I am not there, which would be harder to do in a multi-family in VT, because they usually are not as nice or desirable.

4. The upkeep. I wouldn't have to worry about grass, or the roof, or the toilet not working, etc. 

So what I'm really asking is if anyone has had experience owning a condo in this area and renting it on Airbnb (or other sites). Or has experience owning and house hacking a multi-family in this region.

Thank you!