There's generally less of a "feeding frenzy" and thus more opportunities for a couple classes of property: 1) larger 5+ complexes weed out a lot of first time buyers who don't have the cash or experience to work in this space. 2) "C" ish properties tend to attract fewer offers than solid B+ properties in this market.

, what opportunities for upgrades there are (which depends heavily on the landscape - not just the landscaping), what needs fixed, how busy it is, and what the golfers and hotel guests think of it in its current state.I'd also want to know how much overlap there is between golfers and hotel guests, which business is attracting people to the other (if any), and if one business is helping keep customers at the other despite some shortcoming. 

So far small multifamily is what looks most attractive to me.

This is my first wholesale deal, though, so I wanted to see if 10% off the asking price is enough of a discount to attract investors?

Fixed rate is attractive. 

You are correct that the mechanicals are a mess but that is what attracted me to the property in the first place.

I haven’t been in the area but saw a few attractive properties online.

To maximize the investment, the place should be an attraction for air BnB rental.

Because most Places in the northern half of the US simply don’t attract enough year-round traffic to be profitable in any year, even years 2, 3, 4 & 5 which is when you tend to make a lot of money on investments in the southern US

There are some great ones in your area, and if not, start one, or drive every month to one, you can find them or start one here:https://www.biggerpockets.com/...I believe the best local events for you are the Central CT meet-up in Manchester hosted by Scott Hollister and the Glastonbury meet-up hosted by Stephanie Cabral both great events, hosted by great knowledgeable people who attract a great group you can learn from.Best of luck