Yes.
I skipped buying in 2007, simply because buy-vs-rent numbers did not pencil out. So I continued renting.
I purchased in 2016, because buy-vs-rent numbers *did* pencil out somewhat at that point of time. The NYT calculator told me, based on the numbers for the house we were considering, that we'll do better buying if I stay at least 6 years or more - which is a big thing in the HCOL area I live in. So I purchased this house for $280k in 2016, where it had previously sold for $380k back in 2007, AND was originally listed for $340k.
The reason I could negotiate so hard in 2016 are (not in any particular order):
1. The local market was very depressed as some of the big corps had just announced they were leaving (GE/Aetna).
2. The seller had some unique situations that made them very motivated.
3. The house was almost a "fixer upper".
4. I made a lowball offer (5th offer in 2 months from our shortlist of listed houses in the area) and did not have a buyer's agent - i.e. the sellers agent would get double the commission, making him very motivated.
YMMV, of course.
We moved in right after closing and have been fixing stuff from our monthly cash flow since then.
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Waiting to enter the stock market is different from waiting to enter the housing market. Stock market counts as "investment", while you would be better off in 90% of situations treating housing as a "lifestyle expense".
Even so, I would be very hesitant to buy stocks that are wildly more expensive compared to their intrinsic value. I haven't personally done the calculations - but my gut feel is that expensive housing in some areas would be just as wildly out of whack with it's intrinsic value derived from rents and expenses.
Controversial post by J L Collins, but a great read nevertheless:
https://jlcollinsnh.com/2013/05/29/why-your-house-is-a-terrible-investment/
