I'm not a boomer but I'm a Gen X. I bought my first house in early nineties, a couple more in the mid to late nineties. One in 2007, a few in 2014-2019.
Please note I only own one property at moment. This is my story of buying a house, then selling it to buy the next one and so on. I briefly had two properties at one time but hated being a landlord so went back to one.
The point of the story is I have experienced house buying from the early nineties to quite recently and here is my experience of the differences.
In the early nineties - the country was in recession. I lived in the south east at this time and we stretched ourselves to buy a 2 bed ex council house being sold privately. We were 19 and 23 at the time on average wages. It felt difficult at the time that we could only afford a small ex council house but now I see how lucky we were that at these young ages we could buy in Guildford (very expensive place). Due to a break up I didn't own it long so no gains made. Due to the recession it was very much a buyers market although we were not aware of this being young and probably naive. The house we bought was certaintly reduced but the owners had bought it from the council so I think would still have been making a profit.
My next house buying was during the mid to late nineties in my native Scotland. Outwith the cities properties were not really rented only bought so you were not competing with landlords. The process compared to nowadays felt very easy with lots of choice and when I look back now the prices were laughably cheap. You circled a bunch of properties from the property papers - mostly no pictures just words (3 bed detached, GCH, DG, parking) which seems so little info nowadays to not even know what it looked like when you made the appointment. The agent would send you out a paper brochure which you might get prior to the viewing or you might not. There was a huge selection of houses to choose from and the whole process (compared to now) felt quite civilised and polite. You picked the house, you made an offer, there might be a bit of negotiating but all settled reasonably easily for around what it was advertised for. Prices now for same house around 3 times as much. So it wasn't just the house price that was less back then it was the whole process was much less 'frantic, competitive and lacking choice'
Next house purchase 2007 - sold easily but struggled to find somewhere to buy. This was at the boom before the recession and prices were alot higher and anything good was being snapped up. Bit of a nightmare trying to buy.
Next purchase 2014 - tail end of low prices. Bought tiny run down flat in city but in a nice street. Sold it in 2019 for 60% more than paid. Yip prices were way up again.
2019 - bought outwith city in a more suburban area. Prices felt high compared to a few years before but with hindsight were reasonable compared to the madness of 21-22. Not alot of choice though. Landlords very much a feature of this suburban market compared to back in the nineties when they were not. So much more competition now against landlords and also older people who were over 55 and releasing pension funds to buy properties. Compared to the nineties when only 'house buyers' bought houses todays market is filled with other types of buyers meaning more competition. Difficult to get viewings when properties first came on market (again very different to the nineties) and if you got a viewing you would quite often be getting shown round with other viewers (not a nice feeling) whereas this was unheard of in the nineties.
So from someone who has bought a long time ago (over 30 years ago) to quite recently this has been my experience. The buyers of the nineties were indeed lucky. I look back with much nostalgia at the choice, prices, ease and politeness of the process in the nineties compared to the maniac, stressful, competitive, lack of choice nightmare that it has become.