I dry slipped for a year. What a big god****** hassle. It was an extra 2 hours of work per trip. My bottom was painted when I bought the boat, so it wasn't a big deal for me. In fact we dry slipped it for about 4 months, until a transient (monthly) slip became available. I like to hop in my car and be on the water in 40 minutes.. not possible on a trailer slip.
The dry slip was a serious pain, as it just added steps and hassle:
1) hitch the trailer at the marina
2) load the bait on for the day
3) wait for a spot at the ramp to open
4) launch the boat, while one person has to park the trailer 4 parsecs away
5) sit and twiddle thumbs and get irritated waiting for person parking the trailer
6) fish
7) wait for spot at launching dock, get cut off by some weekend warrior with no courtesy or boat handling skills
8) send someone to get truck, wait 4 light years
9) wait for spot at launching ramp to open
9) land boat on trailer
10) park trailer
11) wash boat
As opposed to my wet slipping life:
1) load bait
2) fish
3) wash boat
My marina is honest and not gouging about fuel, so cheaper gas prices on a road station are negligable. Wet slipping allows me to single hand (fish alone) which would never ever ever ever be possible dry slipping. There is a comaraderie at the marina that we never got dry slipping - and finding new fishing buddies / rivals.
Simply put, I use the boat more. A *lot* more. I can sand and paint the bottom myself (it really is't that much work). We wax the boat once a year in the fall. We keep the boat nice, but not showroom condition - this is a fishing boat, and we fish it hard.