It seems like you're realistic with what you're doing, what you want.
If you want to deal with tubulars, I'd look at HED wheels. The tubulars are light, relatively cheap, and very fast/light. Really fast, like obnoxiously so. The clinchers are the same price but heavy compared to the competition.
You can ride a tall rear wheel in any condition. Front you should have a lower profile wheel and an aero one. You can do long, long rides on aero wheels, and it's fun to be able to dial it up 80 miles into a ride, hearing the wheels hum, etc.
I have less engine than many and I have the HED Stinger 6s and love them. I've been afraid to ride them for training since I don't want to cut the tires at this point (I have almost no spares right now) but I'm sure I'll take them out on non-race days in the future. I'll be buying a Jet 6 / Jet 9 set up (front/rear) for training.
The wider rims on the clinchers are supposed to be more comfy but I don't know. I'm getting them so I don't have to adjust the brakes every time I swap wheels. That and it's good to get used to the way the tall front wheel handles.
Have fun with it.
Not sponsored by HED,
cdr