I'd echo what @DaveP043 said. The Hickory Tavern is a chain here in NC that is a great, typical bar spot. Never been to the Sly Fox, but I've been to Dugan's Pub which is right in the middle of downtown Pinehurst. Always sat in the basement and had a good time and good food. Might be hard to accommodate 12 there though unless you call ahead.
I'd also give a big thumbs up to Etalia.
Sounds like you should get a lighter bag or fix what ever is causing your pain. There are bags with wheels but if you don't have 85 for the skate... I guess you could give the bag worker a couple of bucks to carry it for you.
You ask to borrow one of the push carts just to bring your bag from the car?
Welcome to TST! I'm assuming where you play doesn't let you bring the cart out to the parking lot?
My thought is that it would be really challenging to install wheels on a golf bag and have it last, simply because the bag will not have been designed for whatever weight distribution you end up with.
How about buying a new golf bag that already has wheels like the Sports Spinner?
Alternatively, maybe you could find a hand cart or dolly that would work to get you from car to golf cart.