With all the new fangled lures out there today, do you think the older outdated lures would work better as they're something the fish patent used to seeing? (ie: heddon river runts, etc.)

No better, no worse.

No not really. When the summer evening fishing is slow, I can still rely on my good ole' Jitterbug for a good fish or two.

An 8" black Mann's Jelly worm still catches lots of fish for me. My friends dad fishes almost nothing but an old white and red Bass Oreno and catches quite a few fish on it, not any more than a modern popper but it still works.

Confidence is key, a go to bait is only a go to bait because it worked for you in the past.  While old is a relative term some of my jerkbaits are 22-25 years old and I still use them today, but I do believe there is always a better bait for the job again confidence.