Well, my response will be very different from the two previous posters.
I moved to Florida three years ago from Kansas City. I live in Windermere and I love it. I've found the people in the area to be very friendly. Due to the weather, people spend a lot more time outside. In the evenings, many people are out walking and talking to other neighbors. I like that. When we first moved here, I had to do a lot of shopping and had a lot of deliveries. The people in the stores were so friendly and helpful. All the people who made deliveries were very friendly.
I didn't have much trouble adjusting to the weather here. During the late summer months in the midwest, temperatures often went above 100 degrees and stayed that way for several weeks. The humidity was also high. Since I moved to Florida, the temperature has never gone above 100 degrees. In fact, it rarely goes above 95 degrees. During the summer months, it can be very humid, but the other months are glorious. Sunny and 70 degrees is my idea of wonderful. Very few days of the grey overcast look here. That was the norm during the winter months in the midwest.
As far seasonal changes, we do have them. They just aren't as dramatic as in other areas. During the fall, certain trees change color and loose their leaves. There was a really beautiful stand of maples on WDW property this past fall. It changed to beautiful reds and oranges. Of course, right next to the trees that change, you may see a palm tree or some other type of tree. The ornamental trees that you see with the beautiful flowers during the spring and summer months, tend to stop blooming during the fall and winter. Of course the temperatures change during the fall and winter months. At night, during the winter, the temperatures can get down to the 30s overnight. However, it usually warms up to the 60s or 70s during the day. One night last winter, they came on TV to say it was snowing. Sure enough, I looked out at the street lamp and saw tiny little snow flurries. Of course, they melted before they hit the ground, but it was kind of cool. To me this is ideal. I dealt with ice and snow for over 50 years. I don't miss it. In fact, I could not help gloating a little last winter when my friends were in the midst of a big ice storm. My girlfriend had called to tell me how horrible it had been trying to drive home from work. All I could say was that it was sunny and 75 degrees in Orlando. As for utilities, I pay less here than I did in Kansas City. I have a 2300 square foot home. The highest AC bill I have received in the three years I've lived here is $200. I keep my house at 75 during the day and 72 at night. The houses tend to be all electric, so I have no gas bill. My water bill broken into two parts. The regular water for the house runs me about $35 a month. We are on reclaimed water for the irrigation system. I run my irrigation system two times a week for about 30 minutes per zone (6 zones). The reclaimed water runs anywhere from $15 to $20 a month.
A lot of what you will experience in Orlando depends on where you choose to live. There are very few "snowbirds" in my area. That probably has to do with the price of the homes. Windermere is a very nice, upscale area. You will find a lot more of the "snowbirds" in the Kissimmee and adjoining areas. You mentioned Celebration and Winter Garden. There are very nice areas of Celebration, but it butts up to some very high traffic tourist areas, so keep that in mind if you decide to look in that area. Winter Garden is hit and miss. There are some beautiful areas, but there are also some rather seedy areas as well. Try looking around the Gotha, Dr. Phillips area. The area along McGuire Rd and near Stoneybrook Pkwy are also pretty nice. Winter Park and Winter Springs are very nice areas, but a longer drive to the WDW area. Since your husband owns his own business and wouldn't have to do I-4, you have a lot of options.
I really don't understand the previous posters comment about lack of family things to do in the area. I guess, if you don't want to be near tourists, that could be true. There are tons of family oriented venues in the area. They are not cheap, but I buy APs to places I like and go as often as I want. You could literally eat at a different restaurant each night of the year in the Orlando area. We are only an hour away from each coast, if you like the beach. The Everglades and the Ocala National Forest are also close. Seems to me there are a lot of family possibilities.
Schools are a problem. Some are good, but many are not so good. The schools in the Dr. Phillips and Gotha areas tend to be good. They have just built a new middle school in Windermere (about 5 blocks from my home). They will be building a new elementary school in Windermere next year. They are in the process of building a new high school to replace West Orange HS. I was not thrilled with West Orange HS. DD attended it for one year. It was old and rundown. It was overcrowded. The new high school should help some of this. I put my daughter in a private school for her senior year. She loved it.
IMHO, one of the problems people have when they move down here is that they expect their lives to be like their vacations when they were visiting Florida. That's not going to happen. No matter how many fun things exist in the area, real life will get in the way. People still have to work, send their kids to school, take care of their homes, etc. Sometimes, it is hard just to find the time to go to the theme parks. I tend to go to a park about once or twice a month. I spend a lot more time at DTD just because it is so easy to get in and out. If you move to Florida thinking you're moving to paradise, you may be disappointed. It is a great place to live, but like every other place, it has its problems.
There is crime in Orlando. Some areas have a lot of crime. It is a big city! I feel very safe where I live. IMHO, the biggest problem the greater Orlando area faces is traffic. Now, you will hear from many locals that the traffic problems are all because of the tourists. Don't believe it! There are a lot of tourists on the roads in some areas. Some are even lost! The worst drivers are the locals. Many are very aggressive drivers. They run red lights, tailgate, change lanes erratically and are just plain rude. Everyone is in such a hurry to get where they are going. I try to avoid driving the highways as much as possible.
The cost of living is not cheap, but it is not as bad as many other areas. It is more expensive to buy food here than it was in the midwest. You'd think that produce would be cheap here. It isn't. Real estate taxes can be pretty bad depending on where you are, how old your house is and whether or not you have a homestead exemption. Mine isn't bad. My real estate tax on a home valued at about $500k is about $4k a year. One of the biggest issues right now is homeowner's insurance. It is much worse on the coastal areas than in the Orlando area. Last year, I paid less than $1k for my insurance. Unfortunately, my insurance carrier is pulling out of Florida, so I must find a new carrier. I'm sure that my cost will rise.
Many people worry about the possibility of hurricanes. Yes, we had a rough year in 2004. We had just moved to Florida in time to experience Charley, Jeanne and Frances. One of the reasons there was so much damage in the Orlando area from these hurricanes is because it had been so many years since Orlando had experienced a hurricane. Many roofs were well past their lifespan. Many big trees should have been removed or trimmed. If we were to experience another hurricane now, there would be much less damage because things were taken care of after the past storms that should have been done years ago. I had no damage from the hurricanes. By the time the hurricanes get to the central Florida area, they have lost a lot of their punch. It is mostly a big wind and rain event. Not to take them lightly. If they ever predict a cat5 making landfall at New Symrna or Tampa and heading my way, I will be out of here.
The other posters are correct about the basement thing. I do so miss my basement. My garage has to hold a lot more than it did when I lived in the midwest. It is a good incentive to not hold onto things you don't need. LOL!
So, you will find those who dislike the area and those who love it. I guess it comes down to you personally. Since you say you really love the area you are in and you have family there, could you really move to Florida with an open mind? If not, it may not be a good idea to make the move. If you come down expecting to dislike living here, you probably will. Good luck making your decision!
I don't think I could live in FL year round though. Of course, I think where you live in FL makes alot of difference. We lived in N Miami Beach and DH's bro lives in Vero Beach. They seemed to have a little bit of change of season there.
. It is expensive to live here. DH's job had tranfers to come to FL and no one accepted because the cost of living is almost the same as NJ. 
LOL I was shocked, but loved all the leaves changing color. If you're wanting to keep the seasons, I'd pick somewhere in mid to north Florida.
