Sure, but not as much as old DOS/Win95 games. After all, there is 3D environment, Direct3D graphics acceleration and 1024x768 res. Not great by today's standards, but doesn't look that bad at all. Check the review section at Subsim's main page, there are pictures attached and you can have an idea of how it looks like.
Hardcore: There are many options, so you can go from full manual to full auto on everything, you can customize it to your taste.
Multi: DC2 allows multi against other DC or SH2, though subsim's unofficial Projekt Messerwetzer patch is nearly mandatory for internet play. LAN isn't that bad, though PM enhances it also considerably.
Price: For the price you mentioned you can get here in Spain the combo SH2/DC