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

IMO tubulars are not as difficult to deal with as most people think. There's a bit of a process sure but you get less flats(depending on where you live), the ride quality is superior, cornering is superior and they are actually safer. I can change a tubular flat in less time then i can a clincher but of course you can't high speed corner on your way home. New tires need to be stretched and the gluing process can take a bit of time. Of course there is a trade off but it's worth it imo especially on a stiff deep dish rim I would think. For a long time I trained on clinchers and raced on tubulars now I am like 90% on tubulars. Always have a set of clinchers in case you get lazy though.

my 2 cents.

What about going tubeless?

No glue and you can put a tube in if you have a flat.

However I don't know if you can get nice wheels?

Any thoughts/ experience with tubeless would be appreciated

I've not ridden tubeless, but from everything I've read, it seems like they are most beneficial to mountain bike riding, where pinch-flats are much more prevalent. On road, they will limit your choices on rims and tires....