LIVING IN ORLANDO:
If you are going to buy an existing home understand that the asking price is just the starting point. Unlike other markets, however, you will negotiate up from the asking price. If you are going to have a home built it will be a minimum of a 1 year wait right now. There is high demand and low supply. Most builders have a lottery system. Some lotteries send out an e-mail notice to the folks on their list, and the first people to respond get the lots. Other builders will release lots once a month and you must be at the named location at the named time and date for the lottery. Basically with this second type of lottery they draw names out of a hat.
I bought east of Orlando just south of Oveido. My schools are A and B rated, but with the exponential growth occuring here I don't expect my kids will go to the middle and high school that are currently in my district.
I'm moving from the midwest so I am getting more home for less money than what I paid for in the midwest, but it wasn't as cheap as I had thought it would be. With all the upgrades, lot premiums, etc. I pad over $300K for 1800 sq. ft.
Winter Springs and Seminole County as a whole have great schools, but Brevard County has higher rated schools. Orange County schools aren't rated as high, but they are rapidly improving.
Most of the folks I work with came to the east side of MCO to avoid having to use I-4. 408, 417, and 528 are convient roads to use as a reference for looking for communities.
BALTIMORE:
I grew up in Severna Park. I love MD and wish the wife would move there. Yes it gets cold, but for the most part the winter is mild. April, May, and early June are awesome. July and August are the muggiest, but the Fall is long and mild. It won't get really cold until right after Christmas, and you're out of it for the most part by mid to late March. It's a great area to live in. Baltimore, Annaplois, and DC make a great triangle of culture, food, and fun. There are plenty of good schools, good bars and restaurants, and excellent sailing.
I hope some of this helps,
4lowed