Hey OP,
I grew up not far from you down in L.A. near the coast. I had a typical house for that area (4bd/2ba 1,800 sf ranch) and could go to the beach, mountains, desert, major concert, or professional sporting event on any given day. Things were good but I started thinking maybe there was more out there, especially when the youngins' got to school age. I planned my move for 3 years and then sold my house at the peak before the crash. I took that money to a luxury burb in the South and got a 3-level, 6bd/5ba 5,000+sf colonial for about 60% of the cost of my previous house. I thought of it as a mansion but there it was just like all the others throughout the city. There was a community lake, swim/tennis club as well as all of the entertainment, amenities, and shopping you could want. The free public school bus picked up the kids outside the front door and took them to the top performing public schools nearby. Gas, food, and utilities were all cheaper and professional wages were within maybe 10% of L.A. It seemed everybody had the disposable income and time to enjoy lavish vacations, lake/beach homes, and nice cars and toys. I truly wondered why I didn't make the change years earlier (though the wheeling spots are nowhere near as numerous or nice as they are in the West) ...
...then the first level HVAC unit needed replacement, then the second level and then the third. Next thing I knew it the roof needed replacement on this monster house. One day I'm washing the windows and noticed my low-E double-hung windows and 10-foot diameter palladium window were starting to rot. Come to think of it, everything that wasn't brick on that home started rotting and needed replacement, including the large wood garage door. Oops, that leaky shower pan in the master bath requires enough work so may as well gut the room and rebuild it. Oh, those solid plank wood flooring throughout is nice until it needs refinishing. Aaah, that recalled LP siding on the upper rear part of the house is starting to flake and the blue poly water house connection just popped. More stuff to repair. Oh yeah, there is both a city and county property tax and no Prop 13 to keep it from dramatically increasing from year to year.
The above may sound extreme, but all the neighbors were all facing the same issues. The heat, humidity, rain and cold were just brutal on houses.
Next thing I know the traffic is getting so bad I was thinking I was back in L.A. It was bumper-to-bumper. Aaah, snow was such fun until the city shutdown for a week due to the lack of equipment to clear. Waking up to temps in the teens and scraping the windshield was no fun. Golf ball-sized hail was a hoot as was running to the basement when the tornado sirens started wailing.
After 10 years it got to me; 50-inches plus annual rain, frozen rain, stifling heat/humidity, and feeling like a rat in a maze (tree cover is so dense that it required going in a taller building to see out to the horizon). I realized that I valued the moderate temperatures; low rainfall; proximity to the beach, mountains, and desert; and smaller, easier to maintain homes back in California so I moved back. I did choose to move north of the traffic and congestion of L.A. and feel that I have definitely found the sweet spot.
I guess the point to this long rambling post is that the grass may start out greener forever, or in my case, about 8 years. I don't regret the move one bit and truly enjoyed it for several years but I am so glad to be back and can't see leaving again. I would suggest moving slowly and spending the time to identify those qualities you are looking for in your daily life. Good luck!