I, personally, have never had anything survive very long in one of those pots, and I've tried several different methods. Maybe someone else here has had
luck, but not me.

Following this thread. I just started making one of these. Both bc I had an extra strawberry pot, a lack of garden space, and it sounds neat! From what I read it's best to use low water herbs. I also started with a mix of potting soil and some heavier soil, I think the main complaint is dry out.

Same experience as westelle for everything except maybe hen-and-chickens and even they weren't keen on it.

FataMorgana

I currently have a small one going with thyme in it that I started 2 months ago. It is currently very happy, though it's only been a short time. I have thyme in the top, and the next 2 top side holes. I did have a small thyme that I put in one of the two bottom holes, and it didn't make it. Don't know whether it wasn't strong to start with, or really didn't like the transplant, but it gave up within a week. I used a combo of potting soil and succulent mix. The thyme at the top gets droopy and let's me know when to water. I water a small amount (about a cup) because the bottom does tend to retain water. Right now I have some onion chives in one of the bottom holes, but it was a weak bunch to start with and is kind of stagnant. Don't think it's getting enough sun, as my pots when outside (it's snowing right now) are more crowded than normal with all my veggie seedlings hardening off and waiting for warm enough temps to plant.

Thank you all so much! I appreciate the input!

Watering is suppose to be helped by inserting a tube-with-holes down thru the middle. Even tho it made sense It didn't help for that pot. .

I have several of these (purchased before I actually gardened lol) and only recently am having luck with it. I'm not growing herbs but I think the same method might work for you - I left one opening empty on each pot, and when it's time to water (often in my case since I'm growing actual strawberries) I fill up an old wine bottle and turn it upside down into that empty soil space. This way you're not watering from the top - which inevitably eroded the soil out the holes and onto the floor in my experience. ;)

The water is drawn into the soil slowly and at their roots which also decreases evaporation lost. They sell thingies at garden stores to do this but wine bottles are free around here. ;)

I'm also growing mint in a strawberry pot - as an experiment to see if the roots will find their way out the openings (seems like they should? anyone try this?) And I water it the same way. Some times a little water on top if it's gotten too dry....

Or is this just a pretty thing that dilettante herb gardeners do for four months before realizing that it simply doesn't work?

Yes, especially if you are trying to grow mixed herbs. The vigorous growers will swamp the others. Unless you have one of the HUGE pots, the herbs get rootbound and die.