I've owned two new Harleys. I bought a new Softtail in 95 and a new Road Glide in 2005. I really wanted to give Harley a chance. I sold both bikes within 2 years because while they worked just fine they never made me smile. I kept my Honda V-65 Magna for 13 years and never failed to smile every time I walked up to it, and riding it was always a thrill. And while I've only owned my Valkyrie for about 3 years now I can't imagine getting anything that could replace it. I test rode the new Triumph Thunderbird 1700, and if I didn't already have my Valk I would own a Thunderbird.
If I still had my 1984 Honda Magna, it still would fetch the same price, if not more now, than when I sold it in 1997. Sure wish I would have kept it, probably still be running just fine today although with some fading of paint and chrome starting to rust a little. My prediction is the Valkyrie in 8-10 years from now will be worth as much or almost as much anyways then as it is worth now, but could be wrong with the way the economy is? I too never had one bit of trouble with my Honda Magna except the clutch went out once and 1 dead battery while on the road in 8 years of owning it.
I bet though that Triumph would cost a pretty penny more than your current ride both in terms of price and maintenance cost down the road?
I laughed my _ss off internally when my HD neighbor, who has that HD mentality of ride HD or nothing, told me awhile back he just spent 3500 bucks on a new belt replacement and engine mount that broke when he revved the motor. Some people just got money to burn I guess?