How long had you been there for before it got too long?
Back a few months after 9-11 we did a 10 night stay because three nights were free. The parks were completely empty. Not a soul in sight. The fast pass machines weren't even running. By day six we had done everything there was to do in every park. I remember crossing all the attractions off the maps. That's the only trip we felt was too long. But we weren't DVC members yet, and hadn't yet learned to relax on a Disney vacation.
Our January 2015 stay is an example of the problems of
long-term planning required for timeshare travels. Short answer to your question:
We knew about 2 weeks before the trip started that our reservation was too long.
Since 1996, we've made an annual trek to WDW for a work-related tech conference. Over the years, the pilgrimage evolved into a longer stay (8-10 nights) to allow time for conference social activities, some rest, and some time for transition/logistics. We regularly booked a 1BR unit at BWV and made good use of the full kitchen to support our food preferences.
January 2015:
Having splurged on a large family gathering for a RunDisney event in 2014, we were point-poor going into 2015 but carrying both valid AP and TIW. We booked a
studio unit for our January event at the 7-month reservation window hoping the conference meals and easy access to Epcot would be sufficient to make up for the missing kitchen. Sadly, just a
few weeks before travel our plans/priorities started shifting ... creating a perfect 'storm' of conflicts. If not for 'timeshare' -- I would have simply cancelled altogether. Instead, we flew out, made the best of a deteriorating situation and came home at the earliest opportunity as the conference ended.
If it were a cash reservation at a hotel, I would have cancelled and remained home without any penalty. As it was, the points from our early departure were tossed into holding.
The silver lining: We were able to fully use the holding points for an unexpected, "last minute," Flower & Garden weekend trip in April. So, all is well that ends well ... right?