Hi Kev,
Vera is a pre-fire '02 Bonneville America with 36K miles and no real problems. Never stuck in the shop. Of course there are side stories ... I'm with dinqua: Do maintenance yourself and tool up with the money you save. Trump dealers that have a decent service department are very hard to find (as are any dealership, not just Triumph). Triumph's warranty is rock solid. Two years, unlimited mileage.
Triumph shop charges are 200 bucks for regular service and around 450 for valve adjustments. That translates into about 50 bucks for regular service and 80 bucks for valve adjustments if you use a shade tree.
Step up to Avons or Metzelers for tires. Watch the stock rear brake pads as they wear down quick--7K miles. EBC organics when you change those out. The stock petcock gets stuck and leaks. The Stock handlebar risers might need some spacers. The speedo cable loop breaks after 1 year. The speedo reads about 10% too slow. Your aftermarket options are incredible: Brent at newspeedmaster, Mike at BellaCorse, and Bill at Bonneville Performance, to name a few...Dealers to order genuine Trumpy parts include Bob at Palm Beach Triumph, Florida (usually has an inventory that he can ship out same day) Big4Cycles in Indiana (site sponsor, free shipping) and Team Triumph in Wisconsin.
As far as you purchasing a piglet, ride one first. They are tiny, top-heavy and the 883s are underpowered. Piglets are Lady bikes. Remember that all Hardleys leak oil. (Oil blow-by problems have never been an engineering concern of the Milwaukee boys.)
As far as a Honda Shadow, I am looking for a used one myself. Not to ride but to have as a beater bike. Ride to work, leave in rain, ride it and park it where I wouldn't want to ride and park Vera. But that is another issue.
What to buy? The triumph is a bit more than the Shadow, but you are getting a major bang for the additional bucks. The Milwaukee machines are three times the price of our trumps, with no bang for the additional mula. So whatever you buy, learn to wrench, treat her right and enjoy!