Enve is the choice because of the very good deal I can get on them. I've read plenty of bad things about Enve over the past month or so that would 100% put me off if I was paying full price.
If it wasn't for the deal I'd likely be looking at a set of Flo's or whatever other "cheap" options there are. This is also why disc isn't an option.
I also don't expect to buy any other variations for at least a few years... but we'll see how temptation and budget works out there. I'm thinking if I go for the 7.8 it'll work for the majority of cases, but if it does happen to be too windy I can just throw the stock wheel on the front to get by.
I almost never ride the 808 front, and so far this season, I haven't raced on it (2 OLY races). I just don't feel comfortable riding it in most conditions I encounter with any regularity.
Do you think think the lack of comfort comes from not riding them enough though? i.e. my point around thinking I'd end up getting used to whatever I end up riding. Initially it might be a problem but over time it'd just become the new normal and become comfortable.
We generally don't get that much wind here for it to be a problem in training. The biggest risk for me would be the chance of bad weather in a race... but that's where it matters the most so I do see the problem there. I'll just have to force myself to go out on a normal bad weather day to see how it feels (regardless of the wheel choice). I also have the benefit of being able to stick to pretty flatland on the tri bike and then if I want hills I just head west on the road bike, so I'm not sure I'd have the same descending problems as you being in the bay area.