Road trip: Yes.
Need Temptation to buy more equipment: No. ?
I am following your advice to spend the money on trips to use what i have.
Destin last week.
Edisto Island next week.
Probably Destin a couple more times before the year is over (mid-Dec planned, another one late Nov hopefully based on wind and work).

You guys need to do a group campout/road trip like we used to do back in the day. Those were loads of fun with or without wind.