Repetitive Fields are VERY old technology, pre-Version 3 before there were relationships between files. I seem to remember though that searches were hampered by being tied to first repetition only. I started using with version 3 and I have only used Parent Child record relationships. I think you have hit the wall that is inherent with repetitive fields.
That's a bummer. It would be a powerful ability to utilize repetitive fields in the way I would like to. I wouldn't need to create a new record for each single iteration and I could have a simple layout showing the two fields and their repetitive inputs displayed in full. Creating one at time can be confusing and time consuming.
It really shouldn't be that much more effort to set up a table of related records using a portal or even a "horizontal portal". You still have to enter the individual values either way and you can still: :...have a simple layout showing the two fields and their repetitive inputs displayed in full."--that's what a portal is for after all.
And you gain a great deal more flexibility with the related records approach that was never possible with repeating fields.
But just to be clear, it is possible to do what you want with repeating fields, we just don't recommend that you do it this way due to the many limitations.
A looping script can loop through the repetitions so you can perform a find or use a relationship to get to the year record and then loop to look up the value from the correct repetition.
That's just a lot more complex than a relationship that could take you to the year and the value all in one query of your data.