Well, for starts...Gin Joint (trying not to be hyperbolic) has gotta be one of the best bars in the country right now. As you pointed out, the bourbon list alone is, well, insane. I don't even like mixed drinks (I like my drinks neat), but at GJ I go for the mixed drinks, because they're just that innovative.
If you lived at 55 Ashley, we were basically neighbors. I was at the corner of Beaufain and Rutledge, at Berkley Court Apartments.
Re: Zero George... just a few tid bits to explain why I was so blown away (don't want anyone walking in expecting a StR NYC/George V/your lux hotel of choice). For starters, entry level rooms are small. The place is "comfy" - don't go expecting to pay rack rates and a huge room. That said, the rooms are very well appointed. Everything down to the towels, rugs, cloth used to cover the chair, is very high quality. The bedding is top notch. Again, it almost feels like you're in someone's house...that kind of care was put into the rooms. Also, the "porch atmosphere" was just so welcoming. I'm kind of an introvert, my wife is an extrovert, but free wine happy hour on the porch was just awesome. We both had a blast...it had enough people where you could find someone to talk to, or you could sit alone and read a book. Lastly, the benne wafers they put in your room everyday are one of the best in-room amenities, ever.
The food + kitchen (and its interplay with the check-in process) was so unique, I haven't seen anything like it. Their head chef was literally shaving proscuitto and blanching white asparagus, while front desk was serving us wine and checking us in.
Anyone whose used to staying at nice places know that a "luxury hotel" goes beyond a good hard product. ZG is not perfect, I'm not claiming that. But the sum of all its parts makes ZG one of the most pleasant stays I've had anywhere. I think it's especially nice for someone, like yourself, who used to live in CHS (or who, at minimum, is familiar with the HD). Laugh all you want, but being able to walk to Harris Teeter or even Big John's Tavern (hah) was very nice.
Wentworth has amazing soft product, and it is no surprise how they treated your mom during her MUSC stint.
Vendue is kind of bipolar. Just to reiterate (I'd hate it anyone made the same mistake I made): do not stay in the main house until the refurb is done. Vendue Suites is where you want to be until then.
I try to avoid Charleston in May due to Spoleto. That said, the week prior to Spoleto is a great time to find hotel deals. My favorite times for Charleston are: Fall and Winter (too much pollen in Spring for me).
PM me or keep me in the back of your mind next time you're in CHS. We're there 3-4x a year, and very well may move back there in the near future. Would love to meet another FT'er.