I've never encountered a vintage steel Trek hater and from what I've seen (never owned one) they look to be quality bikes. I owned an aluminum Trek 1000 (hated - unfairly in that it was poorly equipped, too big, entry level) and aluminum Trek 8000 MTb (liked a lot).
I think the love/hate applies more to the modern bike crowd. They are fairly ubiquitous, can be a nice enough bike, but maybe connote a " well it was this or a Specialized". I will admit to looking down my nose at a modern fancy Trek, thinking the buyer could have put more effort into it and gotten something with a little more pinache to it, but hey that's not important to a lot of folks.
__________________
N = '96 Colnago C40, '04 Wilier Alpe D'Huez, '10 Colnago EPS, '85 Merckx Pro, '89 Merckx Century, '86 Tommasini Professional, '04 Teschner Aero FX Pro, '05 Alan Carbon Cross, '86 De Rosa Professional, '95 Gios Compact Pro, '95 Carrera Zeus, ‘81 Masi Gran Criterium, ‘81 Merckx Pro, ‘89 Cinelli Supercorsa, ‘83 Bianchi Specialissima, ‘VO Randonneur, Ritchey Breakaway Steel, Rivendell Rambouillet, Heron Randonneur, ‘92 Ciöcc Columbus EL