It sounds like fair game in terms of different clients such that you are not giving one client two reports on the same visit. I would do two different purchases to avoid possible complaints because it would appear the purchases are specific rather than just a proof of date/time/location of visit.
Actually, there's no way to tell if the clients are two separate clients, if the new MSC is testing to see if the client will switch to them, or what. One MSC has had the shop over a year; the new MSC, this is the first month.
Especially if they're bonused or might be in the future. Or if you really want to continue shopping it. Best not to take a chance on getting blacklisted. Play it safe and, "Keep 'em separated!" I dunno, it was a song.
You know, upon further reflection, if the purchase requirements were different, I wouldn't even have needed to ask the question. Easy peasy -- do one, wait a few minutes, do the other. You know, like some QSRs require only an item off the 1$ menu, more as proof of shop than anything else.
But the purchase requirements are identical, which is what led me to the question. It is, to me, a significant amount of cash.
I agree with the above advice but also think it is probably not legal to get reimbursed twice for a meal you paid for once and take it off your taxes twice. So there is that to consider. But then I do not know the law of reimbursed expenses.
I think it totally depends on the context of the shop. Let's say you get a Publix competitor shop for that MSP. I've done many of these so understand the concepts and requirements. Then let's say you get the other grocery store shop for that other MSP. Questions are different reimbursement is similar but not identical. I would do these two shops together. But in the illustration above, where there was the possibility that the report was going to the same contractor then I see your point. But don't most of us just reinvest reimbursements? I know I do. Reimbursements are not taxable as income, but not really a deduction. Of course, the first year I did thus my 1099 MISC said, "reimbursements". But the last couple of years it just says one lump sum and writing off the gas and home office etc I write off enough to be able to afford my taxes. This past year, with COVID and taking care of my grandkids I wrote off nothing. I only made about 8500k and got a substantial refund.