We have 4 home resorts.
Bought OKW first because it was the cheapest resale buy in in 2006 (at WDW). We have used it to book OKW 5 times (for us, 3 times and for MIL, 2 times) since 2006. SO I'd say about 20% of the time. Not big fans of OKW.
We added HHI, in 2012, after a stay there (using the OKW) and having trouble booking that stay (in July) and we loved it there so we added on for easier booking. We use the HHI at HHI about 95% of the time, if not more. We love HHI and can get there with a 5 hour drive. So we have no problem using our HHI points there so we added on at HHI a second time in 2013.
Then we added on at BWV, in 2014, after a F&W trip where we loved it so much we wanted to go every year and ideally walk to/from Epcot. We use the BWV about 98% at BWW. If we book our beloved BWV, we're are pleased with it and don't try to change at 7 months. We book BWV at 11 months to get the standard view rooms. We like it there so much we added on a couple more times (4 BWV contracts total).
We just, this July, added on CCV for Dec trips. We used the 2017 points for random resies (reallocated points in existing resies that were not at CCV). But will use the 2018 and forward mostly at CCV, likely 98% of the time. Same thing as BWV, when we book CCV (going to book for Dec 2019) we will be pleased and not need to switch at 7 months out.
So, basically, we will stick to using BWV, HHI and CCV at their home resorts but will use OKW for the best option we can get at 7-3 months out (we have BLT booked this Dec). We never really book less than 3 months out, except to change resorts when something better becomes available.