And I don't regret it at all. As for problems, I doubt you'll have many. You're already used to dealing with a housing. You'll need fresh batteries about every other dive. A good charger (less than $50) and a couple sets of rechargeable 1800 mAh batteries will solve that. Instead of film you'll need memory cards. My Olumpus uses Smartmedia and a 128mg card costs me $40-50. I have one card that's had over 1000 pics written and removed to it and it's still going strong.
One advantage of digital is viewing the pics. You can make gross cuts by looking at the 2" monitor but you'll need a bigger screen to make final decisions because you just can't see fine detail in the camera monitor. On a trip you'll want to download the memory cards, if no other reason to see how you're doing and what the pics are looking like, so I'd suggest a laptop. You can always buy several memory cards and just d/l when you get home.
Olympus, Sony and Cannon are the most popular for housed u/w use, with Olympus in the lead. My system...Oly C-4040, Oly PT-010 housing, Fisheye tray, S&S YS90DX duo strobe, MAHA batt. charger and 3 sets of batteries, with various SM cards cost me around $1600 if I was to add up every nickle and dime.
Problems with actually using digital cameras...the only one I can think of now is 'shutter lag'. Until you get the hang of 'tracking' your subject as you push the button, it'll drive you nuts! But all the other advantages of digital far out weigh it. The Olympus, and I'm sure the others, have pre-focus and several other features that will help you learn and manage the lag problem.
I'll not go back to film. I can take over 70 pics per dive (more or less depending on the resolution), I can see those pics before printing and adjust any minor detail I need to (ex. deleting backscatter), and I print only those pics I want. After a trip, I know longer pay $150+ for film developing and start by throwing half of them away. I may pay more per pic for prints now but those pics are keepers and not make dos...know what I mean?
Here's a few of my first...
Taken ambient light only...
Here's a link to my first digital pics taken in
CoCo View Resort, Roatan