All I've ever had was a 4-season tent and I must admit, I'm a bit spoiled by it. Setup takes a couple minutes longer than my friends with their tents which is ok except in the rain which stinks. Same for tear-down. Ventilation is awesome but they can be a tad bit sticky in the summer months unless all the vents are open. I've woken to snow and ice and never felt like this was a bad idea. (Been as low as 19*F for a night or five in it). A bit long in the tooth now at 20 years old, I find myself needing to replace it (
Marmot Sanctum) as the waterproof tape in the interior seams has begun to fail. Not a manufacturing defect, just age.
A strong recommendation would be to get a two-person capacity even if it's just you. Having that extra space for dressing and gear storage is wonderful. I'd also recommend you have a front portico of some flavor - something you can get under if it's raining and then strip, or to stash wet gear instead of bringing it inside. And having 2-person capacity is nice when, well - you have that second person.
Look for some hooks or hoops on the center top interior to hang a small battery LED camp light. That's a nice treat. Side storage netting is also nice when you setup for multiple days in one location.
I think the 3-season tents are just fine as well seeing all my friends with them, camping with them etc. One of the biggest upgrades was a ThermoRest or some similar blowup mattress pad. Doesn't need to be thick as an inch or so is all you need to get you off the ground with an insulative layer. I'd also recommend the longer ones versus shorter. Your legs want to stay warm too, right? And don't skimp on the width. Nothing worse than turning the slightest and falling off the edge. Between the pad and a premium down bag, you should be set for a comfortable night with these two items.
My 4-season tent/ThermoRest and down bag have been my constant companion through 49 states of riding and camping. When you wind up with the right combination of gear, your stress is removed about 'lodging' on the road and you can enjoy the trip that much more.