Part of my husband's C/S to his 1st ex-wife (back before we were married) involved direct payment of her mortgage, homeowner's insurance and property taxes. This worked great, because her earnings are inconsistent and she's sometimes impulsive about spending on things like going out to eat and then doesn't have enough to pay her essential bills. So having my husband do that eliminated the potential threat of their kids losing their primary residence. This also worked well because she and my husband co-parent and communicate well. If something came up, forcing my husband to make a late payment, he would call and warn her that she might get a late notice in the mail, but explain that he would receive a large payment on a contract mid-month and make the payment then and pay the late fee. And she trusted his commitment to fulfill his obligations and would not take advantage of such a situation by having him prosecuted as a dead-beat dad.
What you want to avoid is the situation we currently have, with his more recent ex-wife. She's supposed to pay a form of in-kind child support, but she takes a lot of liberties with it, leaving my husband perplexed about whether to try to correct it in court, or let it go. In all the he said/she said that would go on in court, he will probably wind up looking like the jerk (for "nickel-and-diming" her, after he already won custody), even though she is the one being irresponsible about her financial obligations to their kid.
It's important that an in-kind arrangement be very specific about how much the payor owes; exactly what is to be paid in-kind; as specific an approximation as possible of how much that costs (i.e., how much of the total C/S obligation is fulfilled by that payment) and what the penalties are, for non-payment. It also helps if the couple can communicate civilly, if/when unusual circumstances crop up.
