I used to think and plan this way, upgrade when the market is bad. Now the market is not good but even if you still have a job in this market, you'll be afraid to buy a more expensive house because you just don't know if you will still have a job in three months.
Depending on how much of an upgrade you are looking for, you net gain might be small and your cheaper older house will take longer to sell which will eat into your gain at the end.
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