^Wes - my Dad always said if you really like something, buy 2...you never know if they will stop making it. So I sometimes take it a step further and get 3. I'm glad I did with the boots, I haven't seen them for sale at RL for some time (although I'm sure there will be another run before long either in store or on line) The 'new' ones pictured here have been in the box since '05 or 06, can't remember.
I can empathize with you on the gf issues: when I wear really nice (IMO) cordovan Aldens, split toe cigar, etc...or even MTO dark oak Edward Greens with jeans for example, my gf says: do you have anything other than plain brown 'work' shoes, maybe like sneakers or something, maybe you should try that??
And for work dress the same comment as yours re basically all looking the same. But her other good qualities make up for her disconnect with my shoe preferences.