I was in your shoes two summers ago. Hadn't ridden in 25 years, wanted a bike, used to have a Honda 550, but for some reason wanted a Triumph. I had never ridden on one or seen one other than pictures, but had my heart set on a red and black Bonnie T100. Then along came this red 99 Legend at a local car dealership with less than 4000 miles on it. Like you, I had never heard of the model and I knew nothing about the history with factory fires, new owner, etc., but I did my homework. $3500 later, that Legend was mine, and it is the best $3500 that I have ever spent! Quality is excellent, engine is over built, and as a package, it does everything I want very well. The engine is the real gem, and if you like to do your own wrenching, this is the bike for you! Very old school, and no expensive fancy electronic tools needed. Not that it needs lots of work, but tweaking and maintenance are all there if you want to enjoy it. Although not an advantage over the Bonnie, this forum is probably the best perk of all, as there are some real wizards who hang out here, and basically anything you can ask has been answered, or will be in short order with a post. Not just maintenance, but lots of other good info, too. Get the Legend, it's rarer and not made anymore, and it's water cooled to boot!
PS - Look at the photos of the triples - they are all beautiful bikes!