Join Date: Mar 2006
Location: subject to change
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I think the biggest possible "pitfall" is that you'll never ever want to go back. (We're closing in on 6 years aboard; had to be on land for a couple of months last winter and couldn't wait to be back on the boat, cold notwithstanding!)
Storage may become an issue; most of the liveaboards we know have some kind of land-based arrangement, either a rented u-stor-it, an understanding friend, or a rarely-driven van or pickup. (Work clothing and the paper the IRS demands you store for 3-7 years seems to be the biggest offenders. You'll learn to transfer all your music to an ipod and scan all your photos instead of keeping albums and scrapbooks, for example.) This will aid the dreaded "flat surface syndrome" (junk piling up and the boat getting too cluttered) others have mentioned that keeps you from being able to go sailing on a moments notice.
Here in the land of winter, condensation is an issue for liveaboards during the winter, you may not have to worry about it in FL.
Decide what makes you feel like you're "camping out" and make arrangements to avoid that. For me, walking back to the boat from the marina showers in January with wet hair was a non-starter (for example) so we chose a boat where we could shower aboard.
Trade out your glass dishes for unbreakables and choose your hobbies with an eye to space (model trains is probably unrealistic; digital photography is very reasonable).