My first trip was in the summer of 1987, a couple months before my 12th birthday. My parents had taken us to Jacksonville to visit my Dad's sister. From there, my parents took my brother and I and our cousin to WDW for a couple days and then back to my Aunt's house for a couple more days before going back home. While in Orlando, we stayed at some hotel in Orlando, not on WDW property.
My next trip was in 2000, with three friends from work. We went to Kissimmee over spring break, and only actually spent two complete days in Kissimmee. We arrived Monday evening and left Thursday, so not a long trip. LOL We went to the Magic Kingdom on one of our full days there, and took a monorail ride over to Epcot around park closing time, but didn't get out of the monorail. We just did it for the ride and to see SSE. On that trip, we stayed at the Super 8 motel on Vine Street in Kissimmee.
Next trip was in April 2003 for our honeymoon when I got married. My wife and I stayed in the same Super 8 motel that my friends and I stayed at 3 years earlier. We got 4 day parkhoppers and visited all 4 parks, as well as Sea World and Bush Gardens, and some other things. First time ever at MGM and Animal Kingdom and first time back to Epcot since my 1987 trip. It was my wife's first ever trip to Florida.
Next was April 2004, and stayed at the same Super 8 motel again, in the room right next to the room we were in the year before. Did all 4 parks again, as well as Sea World and Bush Gardens again, and Universal and IofA and some other things.
Next was a brief extended weekender of Memorial Day weekend in 2005. Visited my Aunt in Jacksonville for a couple days before heading to Kissimmee and checking into the same Super 8 motel on Saturday evening. Went to DTD on Sunday, Epcot Monday and then headed for home Tuesday.
Most recent trip was last April, and our first on property trip, staying at Port Orleans Riverside. We plan to do it again this coming April.
So 6 different trips for me so far.