I have an Olympus E510, and I would like to add a couple of comments in relation to your post:
I have also come from the P&S arena, although I used to be more involved in photography a long way back. The point here is, that with P&S (no pun intended) one is used to look at the screen to focus. In this respects, it is a bit disconcerting at first to be without it when moving onto a DSLR. The E510 has a live view mode, which is "kind of" similar to the way you shoot with a P&S. That would imply a familiarity with the way P&S works. However, bear in mind that, with an digital SLR this operation (live view) is much more cluncky that with a P&S. It is designed as an"aid" - maybe - but not as a full-time function because it doesn't work as smoothly as on a P&S. Have a look at Gordon's review of the E510 and the Canon 40D (both with live view) on this website to get a better idea how it works.
Second, as you cannot use the lcd screen in all occasions to compose your shots (like on a P&S), you will have to use the viewfinder. That learning curve - going from P&S lcd screen to viewfinder - is a bit steeper on the E510. Why? Because the view in your viewfinder - what you see - is smaller than the competition's due, partly to the 4/3 format of the Olympus. It does take a while to get used to it. Especially if you wear glasses, that is something to take into account. I found, for instance, that it was much easier for me to look through a Nikon D80 or Pentax K10D viewfinder as they are both nice and bright - especially the Nikon D80's.
You get used to it, and the Olympus has other advantages (for me, image quality, quality of lenses, image stabilisation, live view, size of kit), but it's good if you aware also of its shortcomings. it really depends what's more important to you. For me, for example, the size of the kit, how it feels in my hands, is very important. I had a Canon 40D, and, although a great kit, I didn't "connect" with it. Maybe when I'll be more experienced?...But coming from the "small is beautifull" world of P&S, I feel more at ease with the Olympus.
You also have to consider the camera together with the lens, size-wise. Some camera bodies look reasonable in the shop, with the small-ish kit lens, but add the lens you want, and that baby grows quickly in size! I find Olympus a bit more consistent in this regard, as the 4/3 format translates into smaller lenses also. Altogether, a smaller package.
Another thing you should consider, in relation to you being appointed photographer at your rowing club (congrats!). I imagine that water spray onto your photo equipment will be part and parcel of the job, and hard to avoid. You might want to consider - if you choose Olympus - to buy a superior-built Olympus lens, one that is weather-sealed. The kit lenses you mention are good optically - in fact, some of the best kit lenses you can buy, according to Gordon and others - but they're not weather-sealed. Something like the Olympus (Zuiko, really) 14-54mm like I have (and others in that range) might be better suited to your application (ie with water...).
Finally, what does your colleague - the photographer with experience - say? What does he recommend you do?