Yes, I've booked trips forwards backwards and in-between: dining first, airfare first, room first, dining last, room last, airfare last. I often go to WDW with extended family - so that's a big factor.
Sometimes the airlines don't release the dates until less than 180 day mark, especailly 'sale airfare rates'. So I have to book not knowing what the airfare is going to be. When the airfare is released I may modify our travel plans by a few days. I will also modify our plans if Disney comes out with a discount at less than 180 days.
Usually I book core days, then add as things become finalized. Once we planned on a Friday morning departure, but found it was half the price to fly Thursday night. Once, the airline offered to fly me a day early to avoid a major storm that was exprected to cancel flights all over the country. I didn't actually modify my ADR's, but I booked a room for that one night well after I had all my ADR's in place. (less than 24hours out!)
Sometimes I've done the reverse and used bounceback offers - where I booked a room WAY before I knew anything else.
Mostly, I try to only ADD days. My disney math!

One time, a family member asked to join us about three weeks before we were going! Luckily, I was able to rebook all our dining, and add another room. I think I was only forced to swap one ADR for a different restaurant. I was lucky that time!