I get you. I think there’s an RP element to this.
My players would instinctively have the same expectations as you, due to a long history of playing d20 games. But they also recognise that ‘shopping’ in said systems is dull and some of us actively hate it. I believe the intention here is to cut out the boring stuff and move forward. So I interpret this upkeep rule as meaning that your upkeep expenditure allows you to replace you normal gear. I.e. you have a cuirass and scimitar, but not necessarily the same one. This has the followng implications:
You can usually pick up your characters and just play, without ‘faff’.
In many games, PCs begin with their standard kit, but not the heirloom scimitar they got in character generation.
If ‘downtime’ takes place in a foreign location or a poor location, the exact kit may not be available.
If downtime doesn’t happen, they might have to wait until they reach civilisation or get a chance to replace kit.
Special, ensorcelled or other unusual items can be lost.
This is how I GM it. Personally, I think anything that undermines the illusion of the game should be questioned. Part of the GM’s role is to support your ‘immersion’ in the world, by adapting the rules when necessary. My PCs wont want the kit they lost. BUT if kit is described and given character and is part of the PC story, losing it can still be meaningful, even if its replaced.
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