Ken, when you equate it to cars, you're right on the money!
But. . . .
Yes, the time to buy a 1969 Z28 has passed. Every decade, though, had its gem. Even the smog years. The trick is spotting them, and predicting the future. . . .
In the 70s, the collector car that people were buying and putting up was the 1976 Eldorado~ "the last convertible", GM claimed.
Then in 1983, they reintroduced convertibles! And the value of the convertibles plumetted. Add in the factor that many people predicted their collectability, and this created a glut. . . .
The real collectibles from that decade now turn out to be TransAm SEs (Bandits) and (surprise!) Lil Red Express trucks. Nobody was collecting TransAms in the 70s- every Guido had.one, and they punished the sh*t out of 'em! That's why so few clean ones rremain. . ..
Predicting trends is hard, and sometimes bucking the mainstream gives the best results.
My advice to anyone beginning to collect is this:
1) always buy quality- there are a ton of guys making really nice product right now
2)buy pieces that YOU enjoy. After all, it's YOUR collection~ it's about making YOU happy, right?
Agreed and I see your point.
My point and I seem to have a hard time expressing it.
When few cuemakers were making cues, it was easier.
Let me explain and not sound like a cue snob..

. Because I will use cues that I have or had.
IMO, Rick Howard cues are not collectable cues. Maybe some of the best playing cues out there. But are they collectable? IMO, no. Will they be in the future? Probably not. I love em, owned several but they are not, collectable.
I used to on the Tad M-1, again. It is known as they entry level birdseye cue. Again, maybe one of the best playing cues I have played with. Collectable? Nope. But as Kevin (and Kevin and I seldom agree) mentioned and I agree is the medium and upper Tads to me would always be collectable.
Josswest, by and large most are NOT collectable IMO, especially those he made like Gina "catalog" cues. Now if you had Josswest cues that are NOT on the catalog, I would consider them collectable as they would different.
Southwest cues, I often look at the price these cues bring and shake my head. I have an old JF era ebony Southwest, its a great playing cue, but Southwest makes a ton of cues, and unless it is one of the "fancy" ones, I have a hard time thinking they are collectable cues.
JMO.
So not a snob, just don't think every cue is a collector cue.
Cues that I am surprised that haven't risen in value?
Rambow - I owned one for years expecting values to go up but they really didn't move much. I think I bought one for $1400 and sold it for $2200 or so.
Martin cues - made in limited numbers but really haven't soared in value like I thought it would.
Ken