Unfortunately, you are going to be in for some adjustments moving from a small town to a city like Orlando. You can expect a 20 to 30 minute commute no matter where you're going. There is a lot of traffic and you must manuerver around all the lakes in the area.
When we first moved to Windermere, I drove 20 minutes to the grocery store or the mall and 15 minutes to get gas. Since then, a lot of new shopping areas have gone in, but driving distances is just a part of life here. If I want to go to Winter Garden Village shopping area from my home (which really isn't that far), it takes me at least 15 minutes. During rush hour, it can take longer. Just driving through downtown Windermere, during rush hour, can take 20 minutes. Lots of traffic and only a couple of ways to get where you want to go. You can chalk that up to all the lakes. Can't build roads over them, so you have to funnel around them.
He definitely would not need to take toll roads to get to work from Winter Garden. Once you live in the area, you discover all the back road shortcuts.
Your biggest challenge will be to find a house with more land. To do so, you will need to look at older homes. The new homes have very small yards. Land is at a premium here. Builders try to cram as many homes as possible into their developments.
If land is really important, you will need to go further out.