I've had similar experiences, at one point I ended up giving away a used bike to a mate as a gift, I just couldn't get rid of the thing, new drivetrain, fork, dropper, bars, wheels, the works.
Pre 2020, I was the guy who was able to sell my bikes for close to 80% of what I paid, but that changed when I went up a few price classes. The sub 10k category is still quite strong in mtb/gravel, but the 30-50k segment is under pressure.
I mostly buy used and hold my bikes 2-3 few years while doing subtle upgrades on the used market. But that makes me need an upgrade every 3-4 years as the bike is usually 2 or so years old when I get into it. The depreciation felt by keeping it after that gets a bit much.
My current top fuel 7 has upgraded rims, drivetrain, fork, bars, etc, and I know I'll never see that money again.
When I sell it, I'll make it stock again and take the new bits and sell on the side. Next guy gets a good bike with low km's on the original parts.
That's where one needs to decide about keeping something for enjoyment over resale value, same with motorcycles back in the day, we'd modify and upgrade based on OUR enjoyment and not necessarily resale value for the next Piet.
One man here noted here that prices overseas are worse, he's not wrong. Seth from the Berm peak YouTube channel noted this on his flip bike series. He ended up making very little and losing out often, but that was flipping, not riding and selling.
On that note, I think the days of flipping bikes are gone in S.A, I've been stung trying to build and sell bikes as well. Road bikes are literally impossible to move for a good price as well.
Everyone wants a 11-12 speed carbon race bike for 10k because that 'one guy' was selling his for cheap.
To add complexity, my personal household budget pivot table shows that the my base cost of staying alive has gone up 62% since 2020 (base*1.62), that's literally just food, clothing, fuel, insurance etc.
I can't imagine most people in the country are able to absorb the cost of living increases with the measly 6% most corporate companies give at best per year.
The middle class is under pressure, and the upper middle class will most likely end up buying new anyway. Add to that, the cost of new bikes have become cheap enough that most newbies can get on a decent enough bike for under 50k, why spend 40 on a used one?
Specialized chisel, trek top fuel, merida one twenty, titan cypher, just to name a few.
Cheap enough, and good enough to make a middle class person think twice on buying used.
I think the trick is to buy smart, if one knows what to look for, then one can get great deals and have a good bike under you for longer. But selling that deal you bought will come at a cost to you as well down the road.
In the end, hobbies like cycling are luxury spends, despite them adding value to life, most times you're selling to a guy who's using some of what he has left after feeding his family.
Those making money in this field are making the money on the buy stage of the process, and rarely the sell stage. They're buying low and selling slightly higher if lucky.
