Living somewhere is not the same as vacationing there. With a job and regular stuff going on in life, it is difficult to enjoy it as much as you would on vacation. We went to the parks a lot at first, but tapered off. Now we don't even have passes, hoping for an "absence makes the heart fonder" type of thing.
Orlando has some nice things going for it, but I am not sure how much I like living here. The area is crowded. Traffic is terrible, I find most people not as nice as I am used to, rents and food are more expensive, schools are hit or miss, home prices are okay right now, but overall wages are lower, no state income taxes is nice. Toll roads can be avoided, but at cost of time and gas. Like 10 minutes on the toll to 45 on the roads. It is kind of bland in many areas outside the attractions. I miss hills, it is very flat here. Clermont has little hills. Being able to go all the time makes me less tolerant of crowds and people. When on vacation, my problems were 2000 miles away, but now, I am thinking how we have laundry to do, grass to mow, and I want some time to rest. And then we have to be at a ballgame in the morning so lets not stay late. Going hard all the time isn't the priority. I miss things because I would rather get home than fight the after fireworks crowd. Being a hour from the beach is nice, but like the parks, I find we don't go as much as we would like. The weather is great, lots of other things to do outside of Disney is nice. Diverse population. Some nice outdoor/nature activities to enjoy.
I do have fun when we go to Disney, but there were a few times we just said forget this and left as it was more hassle than fun. Popping in is not as easy as you hope, especially at MK. It takes a while to park and get in. My kids are at the age they don't want to hang with mom and dad too much and have many activities going on, so time is a premium. Most of their friends do not have passes, and I can't fork over $100 just to have a friend along for a few hours, so they often are not excited to go. If you have kids, they may not be as excited to go when living here, especially as they get older.
The app is nice to have now. For ADR's and FP's you need to be flexible. Things open up last minute, but you have to be ready to act. Even texting your spouse to see if it works for your schedule can take too long. And then you have to make it there on time if you book a res last minute. Depending on where you work, it can take a long time to get on property, then park, get to the gate/security, go inside, then walk to the place you are eating, check in and sit. It's tiring. When I say traffic is bad, I mean I drive 7 miles home and it can take an hour or more. All depends on where you live of course, but I4 near Disney is bad for hours almost every night. I would keep extra clothes in the car in case we met up there, but after a day of work, it wasn't always fun to go through all that. We used to be able to book FP on the app on the drive over to the park if it was a last minute decision. One of the reasons we didn't renew is it was not as easy to get a good FP last minute anymore. I started to book FP's for any day I even thought we might go. Jut to try and get good ones, and we often didn't make it. Thats not really fair, but the only way I saw to work it.
Tables in Wonderland is well worth having if you plan to eat at the parks. I'd suggest branching out to resorts more and trying new things. I know I am in the minority, but I don't think a lot of the restaurants are worth it. I mean they are magical on vacation, but not many are really worth the premium price to me. How many times are you going to eat at Be Our Guest or the Yachtsman? A lot of times it is easier and just as nice to go to the place down the street than go to the park to eat. DS is great now, easier to get to with 3 garages, and a lot more food options.
I realize this all sounds pretty negative. To me it is just the reality of living in a place as opposed to vacationing there. Going to the parks on a regular basis is great, I know we will be back at it soon. It just hasn't stayed conductive to my family situation right now. Living here has issues, but so would anyplace else you live in as well. I took a 15 day vacation one time before moving here and loved it, but it is just different when you live in the area.