It's a general useful principle in life that nothing is hard to do once you know how. Some things require more practice and currency than others to feel comfortable. I love flying autorotations but if I haven't done one for a while, the first couple are pretty rough.
That said, there are types which require more practice or a bit of an unusual technique, and in that sense are harder. If you have 1000 Pitts hours you probably think a Pitts is a pussy cat to land, but to any normal mortal it is a serious challenge. (My aerobatics instructor claims the only thing harder to land, or teach people to land, is the U2 - he has plenty of time in both). There are people who claim a 182 is hard to land because it is "nose heavy" whatever that means. I do have 1000 hours in that and I find it a delight to fly in every regard - but for example you MUST keep it in trim, not the case for a 152 where you can forget that the trim control is there and still fly and land it without problems.
When I flew the Pitts regularly I could land it easily and comfortably, but now I only do it a couple of times a year (with aforementioned instructor) and I certainly would not want to HAVE to land it on my own.