Hmmm...
The only Amiga Item I got rid of that I regret very slightly was the 3000T. She was a beasty, and a beauty... Honestly the 3000D is a better fit for my needs, but the tower was rare, with a great build quality, and was the heaviest computer I have ever owned...
Still use my A3000 I bought new in the early 90's. Best darn Amiga ever made, sadly 95% of them have battery damage.
Have my first 500, dead in a box.
I try not too get attached, I generally try a system and get rid of it if my kids or I don't use it.
Seems like an awkward way of just sampling different systems. Do you ever have trouble selling your stuff? I have found it is actually quite hard to get rid of stuff easily.