Dana Point wait list - 30 ft - 10 months to a year. $504 a month slip fees.
36ft wait list - 3 years. $629 a month slip fees. = + $1,500 annual vs 30 ft
+ more $ maint, insurance, cost to buy in good condition, etc.
My 30 ft slip wait time is almost up.
Not sure where in OC you will be settling and/or how far you would be willing to drive, but might I suggest that you consider putting your boat in one of the marinas in San Pedro? I'm at Holiday Harbor (
http://www.holidayharborcm.com/). The rates are reasonable (cheaper than DP), the facility and management excellent, and the sailing is outstanding. Plus, no waiting list for 30 foot slips! You are much closer for trips to Catalina Island. In fact, since you can get there in less than 4 hours you could even do last-minute, quick turnaround trips, whereas from Dana Point, being twice as far, you will probably need to block out more days to make it worth it. (Heck, I've even done trips where I power over in the morning with friends, eat lunch at the Isthmus snack bar, and then blast home on a screaming reach when the westerlies kick in.) Of course, if you are relocating to south Orange County then it could be too much of a drive for your liking; from north OC, not so much.
I had my previous boat in San Pedro (a Catalina 30) and sold it, purchasing an Ericson 26-2 that was berthed in Dana Point. Because the P.O. had already paid for a month of slip fees, I went ahead and spent the first month in Dana Point. I didn't care for it at all. The marina management also wanted me to stay, but I declined. For one thing, there's lots of pedestrian traffic around the marina: people on roller skates, joggers, folks walking their dogs, etc. I think many are attracted by the various shops along the waterfront as well. It always seems crowded, especially in the summer. Plus, the narrow harbor channel is persistently clogged with kayaks and stand-up paddle boarders. I couldn't wait to get back to San Pedro, where the marina is super quiet. (The only people down there are the boaters.) However, while we don't have the congestion of paddle boarders in close quarters there is a significant amount of commercial shipping coming in and out of Angel's Gate. I've never had a problem with it but you do need to stay alert.
From where I live (on the border of L.A. and Orange Counties) the drive out to San Pedro is slightly closer than the one to Dana Point--but in the opposite direction. Actually, for me the closest marinas are in Long Beach, but I don't care for them much, either. (Had a 27 footer there.) So the extra 10-15 minutes of driving is worth it to me.
Good luck with your boat search and finding the marina/slip that suits you best.