Hmmm... I've tried a variety of combinations (get 500 SS then buy, get 1500 then buy, get level 6 then buy, etc.) and the workaround has worked each time. Just to clarify, is this the sequence you are following?:
- Play Gangplank
- Get 500 Silver Serpents
- Open Shop
- Observe that the "Recommended" upgrades are grayed out
- Click on the "All Items" tab
- Observe that the upgrades are now purchasable on the top row of your item grid together with the trinket choices.
Please also make sure that when you select the "All Items" tab, you don't have any filters checked in the store, otherwise the upgrades won't be visible.
If you do that sequence of events and still can't buy the upgrade, please let me know if anything stands out as different for you from what I've outlined. I've tried a few different ways of getting to the upgrades, and the workaround has worked for me each time. I hope that works!