I've done most of the easy HPS hikes in SD county and have ambition for the rest.
If you have a goal to complete them all I would break them down into summer, fall, and winter peaks (based on how hot it gets) as well as leave the hard ones to the end (the all mighty rabbit). Plus most of the peaks in the Cuyamaca and Laguna areas can be done in pairs and triplets, or even has one big group (see:
www.snwburd.com/bob/trip_reports/sheephead_n2_1.html)
If was going to start from scratch I would doing something like this:
Easy Peaks for Summer.Fall
*Stonewall
*Cuyamaca
*Middle (bad views)
*Oakizanita
*Sheephead
*Garnet Peak
*Garnet Mountain
*Monument (some easy class 2)
*Boucher Hill
Easy Peaks for Fall (some cross country involved)
*Combs
*Beauty
*Bucksnort
*High Point (mount Palomar) (Helps to have 4X drive))
Hard Peaks for Fall
*Eagle Peak (a real monster I haven’t done….18 miles and bushwacking)
*San Ysidro
Hard Peaks for Winter (desert cross country)
*Granite Mountain #2
*Whale Peak (Helps to have 4X drive)
* Rosa Point
* Villager and Rabbit
Hope this helps and feel free to contact if you interested in joining forces for any of these.