Buying old bottles, risk and reward?

Auctions-

Bacchus - already mentioned - the best source imo.
J Straker Chadwick, a one-time forum favourite but online only since Covid. Best to go to Abergavenny and collect in person if you win some rather that sort out delivery.
Bid for Wine - individuals list their own bottles via the platform. some bargains, some go high.

There are also several specialist retailers for mature wines. PM if you want details.
 
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Big news today- I see that Berry Bros are launching an auction wing! It'll be interesting to see how it works out - perhaps it suggests that their artificial throttling of BBX by limiting offers to a certain % below 'market' has not been altogether successful which is hardly surprising given that no-one was ever obliged to accept low-ball offers and those who did presumably had their reasons for doing so!
 
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