Hello there, @scbnr.

I appreciate your time in watching our QuickBooks video tutorials in recording business expenses paid for with owner funds. 

To answer your questions, recording a single expense o multiple reimbursement check with different amounts is unavailable because QuickBooks suggests matches to have the exact amount.

You'll want to create a journal entry for this transaction, then decide how you want to reimburse the money. You can check out this article to get the detailed steps: Pay for business expenses with personal funds.

To record a refund from an overpayment, check out this article: Record a customer refund or Overpayment.

I also suggest to consult an accountant to make sure your books are accurate. 

Feel free to message again with your concerns. Take care!