Okay then NorCal will work better. As I prefer cooler over warm/hot.
Have ridden through April mornings in Vancouver and I was okay.
Also live a low key life. Cannot stand too much people/noise either. Hence MilPitas over SJ or even SF.
work is remote so no issues there. Honestly will only “commute” when riding for the sake of riding.
Sorry TMI:
The Bay area has a full 2 seasons of weather that is usually Autumn or Spring and they don't follow a seasonal order that you'd know; North Bay & South Bay have Summer as well! You can usually change seasons by changing locations. For example, if you ever get too hot, head to the coast, it's never too hot on the Hiway 1 PCH which is also really a masterpiece of two lanes from Oregon to Santa Barbara (Subtract in the cities). You can go from 85F inland to 65F on the coast any day. Winter it goes opposite. Inland can be 45F coast 55F as the Pacific keeps temps stable. (IMAGE) The magenta zones are HEAVEN for riding and living. I never got bored with any of it. Hiway 84, 9, & 1 are dreamy in the South Bay. Go to Alice's Cafe on 35 (Find 50 motorcycles at any given moment on Sat / Sun) then head down 84 to Pescadero, then Pescadero Road back to 280. If you do it in that direction the curves are less blind and more fun. Be careful on 35 though it's squidland, seriously. Then rest is awesome.
North Bay Hiway 1, all day every day is magic. Get out before 10AM though at 11: you can play, pass the tourists in minivans. Check out: SF - go over the Golden Gate Bridge to Panoramic Hiway to HiWay 1 go down to Stinson Beach. That'll be a day you'll want to video. Go North on Hiway 1 in the :AM, then South on Lucas Valley Road to go back home, and you'll miss all the tourists. That is balls-out-fun always.
I haven't checked out Milpitas to be honest. SF is really fun to visit, but you have to be really careful riding there. People are from everywhere and you can never count on what they'll do. Hiway 101 SOUTH BAY is to be AVOIDED as if it was on fire. Just don't go there. All the idiots commute with the truckers, packed always.
280 is basically a racetrack, no idea why it's mostly empty, from south SF to San Jose. Occasionally there are cops, but rarely, Sat afternoon maybe. Bikes, Porsches and Ferraris can be found cruising past 90mph any afternoon and they're usually up for seeing who can accelerate.
The only reason San Mateo county exists is to write traffic tickets. If you pass through there, plan on getting one. Years in SF I only ever got traffic tickets in San Mateo ever. Fought 2, won both, paid others ;P Oakland you'll never get one. If you slide sideways through an intersection the cops will ask, "is that the best you can do?" You will see the craziest .... imaginable there.
The Sierras, Hiway 4, & hiway 120 I think were gifts from the Gods. Summer, go there, do that. GO to Yosemite. It will blow your mind. Slow down in the small towns, otherwise you can rip it up. Get to know it a little though. The engineering is predictable until a certain altitude then it goes super random. If you miss a turn up high past 6-7,000 feet, you can find a 1,000 foot drop, so take it serious. June-Sept up there is a dream.