Trying to get a payment every month, is stacking quarterly payers worth the bother?

Know the mechanics before you plan around them, because they are not uniform. Most of the US names I hold pay four times a year on a predictable cycle. Most of the UK ones pay twice, a smaller interim and a larger final, which makes a lumpy year all on its own. Some funds and trusts pay monthly, and a few pay quarterly specifically to smooth things for income holders. If you want a smooth calendar out of a mixed international portfolio, you are fighting three conventions at once.

I built the calendar version, ran it for about two years, then abandoned it for a cash buffer. It falls apart exactly where you suspect: the moment a company you want to own pays in the wrong month you either skip a good business or you buy a worse one for calendar reasons. That is the tail wagging the dog. Twelve months of spending sitting in cash gets you a perfectly smooth income and costs you nothing but a bit of yield on one year of expenses.

One caution about monthly payers specifically: some of the vehicles that advertise monthly income are structured so part of what arrives is not really income, and your cost basis quietly drops instead. Nothing sinister about that, but it means the headline yield and the sustainable income are different numbers and you find out at tax time. Read what the distribution is actually made of before buying something because the frequency is convenient.

Before building anything, spend an evening putting your 40 holdings in a spreadsheet with their payment months. Most people who do this find they are already reasonably spread and the perceived lumpiness comes from two or three large positions clustering in the same month. Fixing those two is a far smaller job than redesigning a portfolio around a calendar. Four of mine accounted for most of the concentration and swapping one evened the year out.

I chased the smooth calendar for a year and the real cost was not the portfolio, it was my attention. I started thinking about the schedule constantly, checking which payment was due, feeling the thin months. Switching to a buffer and a fixed monthly transfer took the whole thing out of my head, and that was worth more than the tidiness ever was.

Smooth the income at the bank account, not at the portfolio. A cash buffer is one decision. A calendar is forty ongoing constraints.