"Worth it" depends on the owner. I more readily do consistent work on my truck because I know I won't get covered in grease to the elbows every time I climb under it. I certainly enjoy any work I have to do much more. This is the result of investing time fixing those leaks. Plus, now that it is clean, anything new that pops up is much easier to trace.
Anyone that can't do this stuff without ending up with no oil pressure isn't following correct procedures or not using appropriate parts. It is actually relatively low risk when done correctly.
That said.. my rig came from Denver. If it didn't have the leaks I decided to fix it would most likely have significant rust problems.