Guess it depends on the chips you're using, the application etc.. I've found sometimes one can do a board with only a few holes, rather large (like CPLD's, FPGAs, uC's) but othertimes, you're right, depending on pinout and external connectors it can just ends up a massive headache. I hate doing via's, because it can be fiddly to get them to a reasonable profile.
One thing I forgot to add, with smt adapters, and stripboard, when you couple those with 'stacking' connectors' one can make quite a good modular system than plugs together, allowing entire 'circuits' to be knocked up, replacing one of those boards. Considering the extra time, and effort designing a PCB to be prototyping friendly, its not 'quick an dirty' but perhaps 'quicker, and 'less pretty'.
One thing I forgot to add, with smt adapters, and stripboard, when you couple those with 'stacking' connectors' one can make quite a good modular system than plugs together, allowing entire 'circuits' to be knocked up, replacing one of those boards. Considering the extra time, and effort designing a PCB to be prototyping friendly, its not 'quick an dirty' but perhaps 'quicker, and 'less pretty'.