I grew up in SC/DP, and worked on the sport fishing boats out of DP in the early 70's-80's.
In general, I think your statement is fairly accurate. There are quite a few boats that are in disrepair. The slips are small, so they have a long term master plan to put in larger ones, but we will probably be dead by then.
But, as discussed, the wait list is VERY long for longer boats.
Overall, I think it is a nice marina, rates are reasonable, and its clean, nice places to walk, etc.
Someone else asked about transferring your slip when you sell your boat. It depends. Most are no, but some yes. Google Santa Barbara if you want to read some drama on that subject.
TLastly, this may not be a popular statement with some on here, but personally I am not a fan of liveaboards anyway, so I don't have an issue with the lack of these. The issues I have had in the past, have generally been living on their boat. But that is for another thread.
We were in Dana Point for the night last week, had a little time, so walked around the marina. I noted a disproportionate number of worthless looking boats occupying some very nice slips in what looks like an expensive marina. What are they doing there? Folks holding a slip until their real boat arrives? No Pride Of Ownership? Get the marina to evict those that haven't moved in a year or two and open up some vacancies?