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I am in the process of writing my will and overall it's a very simple one, apart from one thing: I would like to leave some money for my brother to help him take care of my parents until they die. Once both my parents die, I would like the money to be transferred to my wife or, in case she is deceased, my children.

I am using WillMaker Plus to write the will, and I was confident this was not rocket science and a lot of people need these specific bequests all the time. I am either missing something or this tool is extremely simple, borderline trivial. All I can write is a basic chain of beneficiaries and specify some bequests, but nothing much further.

I understand I could set up a trust to do this and elect the trust as my beneficiary (is that maybe what I'm missing?), but my conditions are very simple in my point of view, and the relationship between my immediate family and extended family is excellent, so I would not like to have to go through the hassle of setting up a trust.

Your wish is to leave money to your brother to help him take care of your parents until they die with the condition that any balance of the money to be transferred to your wife or, if she is deceased, to your children.

The fulfillment of this wish will depend on your brother honoring your request should you predecease your parents and then your parents pass on. Though not a lawyer, I don't think that there's anything in a will that will prevent your brother from keeping the money once he has possession of the money in question rather than passing it on.

If you set up a simple revocable trust, you can include in its will any conditions that make sense. You can dole out "X" dollars per year to your brother until your parents pass. You can write any kind of self adjusting formula that amuses you.

You could name your brother or wife or any other trusted person (family friend, lawyer, etc.) as the executor. If your estate is large enough (perhaps low to mid six figures), the trust department of your local bank can be named executor and it has a fiduciary responsibility to carry out the will's provision.

The short answer is that you should consult with a lawyer to find out what options are available to you and what, if any, limitations exist.

See a lawyer who specializes in Wills and Estates. The problem is that you don't know what you don't know about this subject. They can foresee the problems which may be created by your amateur will preparation. Don't leave a mess behind as your legacy.

I agree with the above that a simple will won't accomplish this, but see below for a way a will could work. I'll quote from the Wikipedia article on trust law to hopefully make the situation clearer.

A trust is a three-party fiduciary relationship in which the first
party, the trustor or settlor, transfers ("settles") a property (often
but not necessarily a sum of money) upon the second party (the
trustee) for the benefit of the third party, the beneficiary.

In this case, for the amount you want to leave for your parents' care, you're the settlor, you need to pick a trustee, and your parents are the primary beneficiary, and your wife is the contingent beneficiary, your children contingent to that. It is very common in trusts to have various contingencies

So it's not rocket science, but it is complicated enough that you're going to want to get some advice on how to handle it the best way. Issues include who would be the best trustee (corporate or an individual such as a family member), the amount to fund to this trust, and the different jurisdictions.

What gets confusing for people is that even when you have a trust you have a will too, that at a minimum pours over any assets that weren't funded into the trust before. The will is also the place to name guardianship for minor children. Also another option to avoid setting up and funding a trust now is to make your will a testamentary will that sets up a trust once you pass. This could avoid some issues in this case and is usually cheaper than setting up a trust.

Lastly disclaimer this is based on experience in one common law country, and you didn't state the countries involved in your case so again, it's best to get some advice on your particular situation.