To move or not to move?

My husband (then boyfriend)and I moved from Washington state to Indiana on more or less of a whim. We had been dating a whole 7 months. We knew we would be together and get married but wanted to start over somewhere fresh for ourselves. So we packed up the cat and the dog, sold whatever wouldn't fit in half of a 24 foot moving truck (the other 12 feet was filled with a car) and headed approx 2300 miles across the country. 7 years later, one house purchase and one daughter later we are, I think, ready to move again. Most likely to Florida. There are so many questions and I hate not having all the answers. I do know a few things:

1. My house is too big. We bought it for a great price, had been living for almost a year in just under 900 sq ft and wanted some space. So we bought as much as we could find. Now a two story house with a full basement and large sun room is WAY too much space for two adults and one child. Our daughter will be an only child so there is no reason for four rooms.
2. I'm a terrible housekeeper and I have zero motivation keeping up 3000 sq ft. I need 1800 MAX to manage even then I know it will be tough for me. I have come to terms with my slobby ways but I want to change, really I do!
3. If I have to spend one more frozen winter in Indiana I may need to be committed.
4. I know that we will face a lot of the same problems in Florida as we would in Indiana, but they will be all new issues and annoyances to contend with, sometimes just a change of scenery is whats needed.
5. Yes I know it's brutal hot in Florida during the summer. But I will trade that for not have to chip the ice off my mailbox to open it.

Things I don't know:

1. Will our house sell in this market? It's an older home, we have remodeled the kitchen. But there are some houses in our neighborhood that have been on the market for over a year.
2. Will my husband be able to find a job? He's in a fairly specialized field which can be a good thing and a bad thing.
3. What will my family and friends think of us moving again. Even farther away from them this time.
4. Will I ever be able to downsize all the crap and furniture we've accumulated over the last 6 years so we can move and not drag our "baggage" with us.

I'm trying to research homes, areas, weather and decide where we want to live. I'm selling anything I can get my hands on in the house. What doesn't sell I will donate. And in between working, a 19 month old toddler and husband who works full time I need to de-crapify my house, pack up everything that can't be in it for showing, scrub the house top to bottom, finish all my half done painting projects and re-stage the house to get it on the market. Oh did I mention I have house guests coming for most of May?