Maura, I could feel your headache in this sentance:
"4) Given that the generalization are based on a calendar year when most, if not all, orchids bloom in early spring, begin active growth in late spring-early summer, and set buds at some point thereafter, do I need to have 75 different calendar years, based on when mine are blooming?"
If this is the case, my Rth. AhChung Yoyo Little Goldfish, which blooms 3-4 times a year, is aging in dog years. I can just imagine you've been reading some lovely, but vapid, Orchid coffee table book. Some of the general advice you see becomes completely worthless when extrapolated over thousands of species and hybrids. You are going to love the culture information on OrchidWiz when you get a chance to get it running.
Many orchids suitable for home growing don't have a true dormancy and others that might have a period of slower growth may abandon that trait altogether under artificial lighting in indoor climate control. Unless you have certain dendrobium species, catasetums, cynoches or other more obscure species, you probably don't need to "rest" them. It might be easier for you to post your growlist and others can tell you if any of your orchids needs a dormant period.
From my tenure as root killer, I can attest to the importance of #3 in Geoff's repotting criteria. I used to routinely repot every new orchid immediately, whether it had new growth or not. Now, unless I absolutely can't maintain it in its media, I wait until I see green root tips or new growths emerging. A growth phase is key to helping the orchid acclimate to its new pot environment. "Springtime" or "after blooming" don't seem terribly critical to most types.
Geoff, have you stopped fertilizing? Switched to a time release, like osmocote? In my opinion, "optimal nutrition" is a fairy tale, whether for plants, companion animals, or humans. There's thousands of additives and micronutrients and different NPK levels and different plant requirements in different environments, it's simply impossible to get it perfect. But, I have a few vandas in empty baskets and several encyclias that seem happiest in lava rock, so I have to feed them something. Can the water absorption and nutrient uptake processes occur simultaneously?