Nice vacuums! I grew up with Kenmore canister vacuums and an upright, so they tend to be my favorite vacuum based on that.
I remember seeing a dark green version of your teal one at Sears as a kid, on clearance for $99. I tried to convince my parents to let me get it with my birthday money, because I really wanted my own Kenmore.
Fast forward to 2012 and I finally got my own Kenmore canister, a red Progressive on clearance at a Sears for $99. Ironic I guess.
I really like your gray Whispertone. That was TOL in its day and has the nice Ametek Dual Stage motor. My aunt I believe still has hers she got in 1993.
I like your Crossover too. I wouldn't mind having that or the Plush model.
Patrick, I like your purple canister too. I've looked at those Crossover uprights. There's been that model one at my Sears that was a return for a while, and they keep marking it down. I've been thinking about getting it if it stays long enough to go under $100.
As for mine, I own the red Progressive canister, a lime green one I got on sale for $99 but its still in the box. I also have a Sanyo made straight suction one from 1983. I've always wanted one of the avocado Sears Best ones with the woodgrain top. But they're rare anymore. I also have a sky blue 2005 jellybean model but it's not in great condition. I might donate that one.
My mom still has her 1999 Whispertone in hunter green and its still going. I repaired the power nozzle socket and it still gets used regularly.