Long time since I ran a 429 but I agree with Bigblock - this is not likely an oil supply issue. More likely an alignment issue with those guides in my view. I never used guides on any of my 429's incidentally. Interesting the wear is only on one head - perhaps check how the guide is fitted on the good side for comparison??
Also as mentioned by someone else, be careful not to pull out a lifter when taking out the pushrods. They normally require a jiggle to break the oil suck. 5/16 diameter should be fine for your replacements. As you have aftermarket rockers it might be worth checking pushrod length before you order new ones - you never know!!
Dax with 1964 Dual Quad 427 and Toploader box
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