I've done tipsy pots for several years now and really like the vertical look. I do have trouble with getting anything to really flourish in them and am not sure why. I've used petunias, rose moss, and a couple of other flowers over the years, but they all seem to fizzle out before August. Have not tried herbs or vegetables before. I use 8" pots and am thinking about going with bigger pots next year.
I always have trouble with the dirt washing out when I water, so the suggestion to use pea gravel is great. I will have to try that next year. One year I used the spaghum moss and the birds loved it so much, I didn't have any left!
This is the best picture I have of mine.