How do you handle this situation (annual gifting to DILs/SILs)?

If gifting to children with a spouse the order should be made out to both of them. I would never exclude their spouse, ever.
This is an interesting take.
I discussed this with a son & DIL (who has a psych degree) to get their opinions, specifically in regards to naming contingent beneficiaries on account where the primary was a son/daughter.

The DIL was adamant: "Inheritance follows the bloodline. Grandkids, yes. Spouse, no. Children of the spouse & previous husband, no."
 
We are helping our only surviving Child, our Daughter who is a Single Mom.

We are gifting with a Warm Hand and happy to be able to do so.

When our Son was alive, we helped both our Son and Daughter out. Not equally but pretty well whatever was needed.

Folks have all kinds of opinions on this matter and the only right answer is what is right for you and yours.
 
Rather than gift to our kids, we bought homes/Condo's for each and they pay us the carrying costs: HOA, Taxes, insurance, etc. The homes are in our name but will transfer to a trust for each child on our death. We initially did this for our oldest son when he was 18. Basically he was too wild to stay at home, or even to keep from being evicted while renting, so it was pretty much either that or he would be homeless. It's been a source of stability for him over 10 years now. It worked out well enough that we bought a place for our youngest when he went to college - he is still there, now in grad school, and for our daughter once she settled on staying some place for at least a couple years. Not sure how well this will work in the long term, but it has been ok so far. I will say that I know way more about HOA's and have far less respect for them than before.

If gifting to children with a spouse the order should be made out to both of them. I would never exclude their spouse, ever.
Interesting. I take the opposite view. We take care of our children. They can take care of their spouses. It's one reason we keep the homes in our name (taxes being another), and then transfer to a trust on our death. If the marriage doesn't work out, an ex spouse isn't getting 1/2 of a home we bought. Seen way too many people mingle funds only to see an ex or widower take ALL the money and the bloodline children be left with nothing. That said we don't charge rent to our children's partners. Our kids pay us the carrying costs and they sort it out with their partner.
 
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8 years ago, we gifted our DD and her husband 100k, between the end of one year and the beginning of the next. We did NOT write “A” check with both their names. Rather, having been audited before by our dear friends at the IRS (and coming thru it just fine) we have been very careful with how we gift. So 8 checks in total were written. 4 in one year, and 4 in the next, just 10 days apart. Two checks each time, from each of us, written to DD and DSIL. In the memo line it said “gift from mom” (or dad). We did this to stay within the gift exclusion, and make it very clear should there be a tax examination, who was doing the giving and who was receiving. We gave them that much so that they would have a sizable down payment on a home they were to purchase. This past Christmas season, we did the same thing again, in an amount that would stay under the gift exclusion radar, but sufficient to pay off their mortgage (since we had a great year last year). Those two are the responsible, hardworking ones. We have a son, whose life is much less stable, works only part time (his wife is in the military) and who has not yet decided to buy a home, and who would waste the money if we gave him a chunk that size. When and if he and his wife do finally settle into buying a home, we will help them as well. Finally, DS is not aware of our wealth, nor did we make him aware of the gifts to his sister. The reason for that can be deduced from the above.
 
8 years ago, we gifted our DD and her husband 100k, between the end of one year and the beginning of the next. We did NOT write “A” check with both their names. Rather, having been audited before by our dear friends at the IRS (and coming thru it just fine) we have been very careful with how we gift. So 8 checks in total were written. 4 in one year, and 4 in the next, just 10 days apart. Two checks each time, from each of us, written to DD and DSIL. In the memo line it said “gift from mom” (or dad). We did this to stay within the gift exclusion, and make it very clear should there be a tax examination, who was doing the giving and who was receiving. We gave them that much so that they would have a sizable down payment on a home they were to purchase. This past Christmas season, we did the same thing again, in an amount that would stay under the gift exclusion radar, but sufficient to pay off their mortgage (since we had a great year last year). Those two are the responsible, hardworking ones. We have a son, whose life is much less stable, works only part time (his wife is in the military) and who has not yet decided to buy a home, and who would waste the money if we gave him a chunk that size. When and if he and his wife do finally settle into buying a home, we will help them as well. Finally, DS is not aware of our wealth, nor did we make him aware of the gifts to his sister. The reason for that can be deduced from the above.
In your trust/will, did you adjust so that your DS would receive the same amount that you have given to your DD and husband, if you were to suddenly pass away? It seems to be fairer that way?
 
We have gifted large sums to our two children, to pay for dental school for one and bought a house for the other. And then occasional $5k here or there. My son lives a little over a block from us. He wants to build a 12ft x 20ft shed. I want him to build a pole barn with one end a two car garage and the other end a shop, So, I can move my tools there, :) he will get them anyway! I'm thinking about gifting him the money to build it. The house does not have a garage, he wants to tie the garage/pole barn into the house, but so far, there is no feasible plan, we need an architect to make a preliminary plan to see if it can even be done, we have a roof line problem, but maybe it can be solved. and he wants to be able to walk from the garage straight into the house.
Also, he has a live in girlfriend, a little talk about marriage, she has some debt, i don't know exactly, but $10k to $20k, if they do get married, I'd like to pay off her debt with the idea, she never goes into debt again.
 
We give each child a check for the same amount of money - 2 of the 3 are married and the check is made out to both of them.
 
We try to give equally to each child, although one has medical issues, so it may not actually be exactly equal. As to giving to DIL, we first gift the maximum to our son up to the limit without getting into reporting on tax return and then the same to DIL, although we might or might not get to the same amount as to our son. As to son and DIL, they both enjoy the $s so designating one or the other probably does not matter.
 
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