I suspect the biggest shock you'll get when switching from film to digital is how slow the digital cameras is compared with the instantaneous response of a cocked film camera. Until you get the rhythm of it you'll miss action shots.
Then there's the cycle time between shots -- again nothing like the speed of manual wind, let alone motor drive.
Doubtless, the more you spend the better the performance in those areas.
Another issue is power consumption -- with a film camera I used to change the battery every couple of years but with digital you're best carrying a spare set of rechargeables.
If I were you I would concentrate on models that best address such issues initially and worry less about image quality -- on the best DSLRs the quality can often be better than film, albeit with a different 'feel'.
The other advantages such as instant confirmation of results and the lack of processing time/cost make up for most of the drawbacks. So, sadly, I find myself almost always using my cheap digital compacts in preference to the wonderfully engineered Canon F1n and Leica IIIG cameras I spent a fortune on 25 years ago. One reason I won't spend serious money on a digital camera is that while my Leica has proved a great investment and the Canon probably held its value pretty well, digital cameras are evolving so fast that most are worthless junk within a few years.