If you persist past level 60-something when Chase begins asking you for 4 million sP items, but only gives you a couple grand in return, do you eventually recap the losses? Does he begin to pay you what you're owed again? Thanks.

No, you do not recap the losses.

The only things you'll get for completing Item Hunt are the achievement and the Swashbuckle that goes with it (which is pretty valuable, but probably not enough to recover all the sP you spend getting there). If you don't want to lose sP from it, I would recommend not doing it, if those other things aren't enough motivation for you to want to do it.

If you're playing Item Hunt for profit, it's best to start over when he starts asking for those pricey items (especially since Item Hunt can only be completed once). If you're going for completion, then it's generally seen as an investment since Chase's payments don't make up for the amount you end up spending on especially the last few levels

OK, thanks. I was going to get the hidden challenger, but maybe not....

I guess it depends on what items he starts asking for, but you only need to get to around level 76 or higher and then quit to unlock Chase. I don't remember it being super expensive when I got that far, but it has been a while since I've done Item Hunter quests so maybe he asks for more expensive things now, I dunno.