You need to do your own research by going on AIR and VRBO and comparing similar rentals during different times of the year, and different lengths of stay.....Other than that, sounds good...you say you're already aware of the pitfalls of HOAs, so if the price is really that good, go for it.....

Get a reliable quote on the cost to fix it up completely and compare that + closing costs + commission + what you paid and see if you can come out on top now in the market.

I'm also from New Jersey, lived in Journal Square area in Jersey City and now I'm in West Houston/Katy, Texas.I am not sure how the prices are in Central New Jersey but I reckon they must be a much more expensive market compared to here in Texas.

Am I correct in assuming I should contact the current owners of the comps and get that info from them, and if so, what are key things to compare?

The answers are quick but you must ask the right people, ask a lot of people then compare and confirm for yourself afterwards.

There is another cabin in that same resort community that is comparable in terms of condition and is slightly larger renting for about $100 per night on average.What questions should I be asking myself?   

This really bugs me when I'm trying to use sites like Zillow or Realtor.com to compare comps in a certain area.

Comparable house B rents for $2,350. 10% management fee = $235.

I believe La Pine is in the path of growth for the Bend area and prices here were 100k-200k less for comparable homes.

I’m aware of some concerns such as lack of equity compared to a normal home, etc.