I sold my Amiga in 1996 and I didn't have any regrets at the time. When WinUAE came out I missed the apps and shit so I bought an Amiga 4000. Best thing I ever did.
As for the future buying off an Amiga...I dunno. Heard so many "big ideas" about the Amiga since Commodore went tits up that I'm of the opinion that they are moving away from the hardcore supporters and getting to the state of the PC.
I don't think this will work, hard as that is for me to say.
An Amiga 4000 went of ebay a week ago for just over £200, while you can get a brand new 1200 for £100. I'd stick to one of those personally.