I had a S&S MMIIex for several years before upgrading to digital and I haven't regretted it at all.
For about $1500-1800 you can get an Olympus C-5050, PT-15 housing, S&S YS90DX strobe, tray and strobe arms, extra memory and batteries. After that you'll have no expenses....no film to buy, no developing, etc. And you'll get instant feedback so you know what your pictures are looking like so you can correct any mistakes while you still have the opportunity to replace them. It makes the learning curve alot smoother.