The changes haven't been drastic since you were there, but there have been some. More so on the Placencia peninsula than Caulker, I'd say. The biggest change in Placencia is that the peninsula road has been paved -- amazing difference! Lots more condos up and down, and some McMansions, including a bunch toward the north end of the peninsula. But the village itself isn't that different once you get off the road.
Caulker has added quite a few hotels and restaurants, but it still has sand streets, few vehicles and is still laid back. The feel is about the same. Just somewhat busier and more expensive.
I don't know San Felipe that well but just driving through from time to time it doesn't seem to have changed much since the early 1990s.
Roads are generally better. Can't remember offhand when the Southern Highway was paved, but I believe the paving began in 2000 or 2001 and final short unpaved section was completed around 2010. That has made a huge difference down south. The government is working on a road from the Southern Highway near PG to the Guatemala border.
The Hummingbird Highway was resurfaced in the 90s, don't recall exactly when.
Northern and Western Highways (now, respectively, called Philip Goldson and George Price highways) are about the same. There is a paved bypass around Orange Walk Town. The Boom Road bypass around Belize City passing the prison to Hattieville is now fully paved.
Don't think there's been any change in the road to San Felipe. There is now gravel road from just south of Orange Walk Town to Shipyard and eventually connecting with the road to Lamanai and Indian Church. The roads northeast of Orange Walk toward Little Belize, Progresso and the Shipstern peninsula and Sarteneja have been upgraded a little but are still mostly unpaved.
There are now three water taxi companies to the cayes from Belize City, two from the old Marine Terminal and one from nearby at what is called the Brown Sugar terminal near the Tourist Village.
--Lan Sluder