Worth it? You ask this of a group of airplane owners? Seems a bit like asking hotrodders if they get good gas mileage...
If you live west of Kansas, I think it is VERY much worth it. Turbos make many many trips possible for me that would otherwise be scrubbed due to the combination of high tops, high MEAs and ice. You eastern guys have it much easier I am told, I guess the tops are very frequently a 8K or below during icing conditions (how would I know, I'm not going to fly someplace where it is snowing on PURPOSE, so I don't go east in the winter).
I think the speed thing is mostly a wash. You go faster westbound, but you burn more fuel coming back east at low altitude.
I have owned four normally aspirated airplaned (2 Grumman Tigers, C206 and C337) and three turbocharged airplanes (T182RG, T210, P337). I think the difference in maintenance is overblown (get it?), especially when comparing turbocharged and pressurized. Yes, turbocharged 337s (and other airplanes) do cost more to maintain. They use up more cylinders, on average, don't get to or past TBO as often, you have more exhaust system maintenance and tweaking, and once in a while you get to replace/overhaul a turbocharger. Overall, engine maintenance is on the order of 15 to 20% more expensive.
But it is WAY worth it. Especially pressurization. FL190, looking down at 16,000' tops, that's a beautiful place to be on a winter day in the west...and no cannula, no mask, no oxygen refills.
My two cents.
Kevin