My wife and I are divorced. She would like to pay the bills and have me reimburse her. I want to make any medical reimbursement checks out to both her and the party who billed her. Can she then endorse the check and mail it to the hospital or billing agency for them to also endorse and deposit? If so, how do I write the "Pay to the order of portion" properly?
What you have described can be done. You would make your checks payable to "EX WIFE AND OTHER PARTY", where the OTHER PARTY is the hospital, billing agency, medical office, etc. Your ex-wife then endorses the check and delivers it to the other party.
Although issuing multiple payee checks in this way is legal, it is falling into disfavor. Before proceeding, your or your ex-wife should check with the other parties involved to see if they will run into any problems depositing checks written in such a way. Banks are becoming more reluctant to accept multiple payee checks for deposit due to perceived increases in the risk of fraudulent endorsements.
If those payees can't accept checks drawn as you've described, you and your ex will have to figure out some other way to handle the payments. One suggestion is to agree to reimburse her on the basis of bills marked "paid" by the hospital or other medical facility.
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What you have described can be done. You would make your checks payable to "EX WIFE AND OTHER PARTY", where the OTHER PARTY is the hospital, billing agency, medical office, etc. Your ex-wife then endorses the check and delivers it to the other party.