Yes, you have to start at the "minors" to get to the "majors" (unless you were military), but I think it's a testament to how safe air travel is today when you see the sheer number of takeoff and landings completed without incident every year. Unfortunately they don't let you start in the 747 and move to the Dash-8.
No, they usually don't. But some airlines have been dealing with the issue by requiring that captains on commuter aircraft serve X number of years on the type instead of accumulating X number of hours before they can apply for FO positions on larger aircraft, so that at least one crew member is reasonably experienced. As the largest modern turboprop, the Dash 8 is usually the last step leading to flying jets such as the CRJ, MD80 and 737. However with some airlines now flying only one type (for example Comair's large fleet consists solely of CRJ's) the presence of experienced pilots even on small airliners is much more likely.
With salary based on seniority rather than type there is less pressure to step up to larger planes as fast as possible like it used to be the case, and there were situations where airliners were being flown by pimpled pilots barely in their 20's who knew how to fly the plane, obviously, but had limited experience in dealing with in-flight emergencies. The Air Florida crash in '83 is a good example of this even though pure stupidity stemming from youthful cockiness appears to have played a role in that specific accident as well.
Even more blatant was the crash of a Pinnacle Airlines CRJ during a repositioning flight (which means that fortunately the plane was not carrying any passengers) where the two young pilots, freshly graduated to jets after flying turboprops for a few years, simply decided to rocket the plane up to 41,000 feet (its maximum ceiling) just to see how fast it could get there. Disregarding all manufacturer directives on rate of climb and breaking several FAA rules in the process they climbed at a vertiginous rate and reached the lofty altitude within a few minutes, where they proceeded to congratulate each other, after which both engines quit because they were oxygen-starved by the way too steep climb. Not surprisingly, the crew was unable to restart them and after gliding more than 100 miles the jet crashed short of the runway they were attempting to reach (missing a house by a few feet), killing them both. Most pilots and other aviation experts were apalled to learn during the investigation that these guys had even thought of attempting to climb at such a rate, knowing that any high-bypass turbojet engine (the type of engine used by all commercial airliners) cannot sustain such a drop in available air oxygen in such a short time without starving. Yet these were licensed airline pilots. Licensed, but not experienced. Had one of the two been flying jets for a little while he would have known better.
Also the Beech 1900 crash in Charlotte a few years ago is said by some pilots familiar with the type to have been recoverable but those who say that weren't there so it's difficult to tell. What seems likely is that if the crew had lowered the flaps and extended the gear when the nose went up the ensuing dive *may* have been recoverable *in theory*.
Even when a crash is not directly caused by pilot error an experienced individual has a better chance at identifying the problem and attempting recovery than someone who's never had to deal with even a minor emergency. Hopefully the FAA will eventually enact directives to mandate that at least one pilot on each airline crew be fairly experienced and paid accordingly.
Note: this post consists of general considerations and does not specifically concern the Dash 8 crash for which not enough info is currently available to comment on.