You are filtering in cupertino/sunnyvale and PA? Those are 2 quite different areas. For 2.5 you can get something thats move in ready ~2000sqft in sunnyvale/cupertino. In PA, you can get a teardown or a house < 1500.
The same discussion has been had almost every fall. It’s a seasonally weak time to sell with not many buyers looking. If you want top dollar, sell in spring. If you want to bargain hunt, buy in fall/winter.
Well this is because we are in a bull market for RE. Any time you buy after 2009, if you wait 6-9 month and sell, you would have made money. It is straightforward now, but once the music stops, there will be a lot of pain.
I bought my primary in Sep since i didn’t mind move my kids to diffrent school shortly after school year started.
However, i bought my rental in June since i didn’t want to list it after summer season. Once you list your rental in fall/winter then it is hard to break that cycle IMO.
No Airbnb (i am pretty picky in selecting tenants).
IMO, the best season to buy is late summer/early fall. Even in winter, it starts to pick up. That means i have to wait quite long time until peak summer rental season.
Anyway, i bought it because i was happy with the location(on quiet cul de sac yet close to bus stop which is connected to Diridon station), house condition(newly updated) and schools and it was within my budget. Now that i plan to hold it forever and pass it to my kids, i guess that was good enough to buy.