Hmm... I have a pretty benign taildragger/tailwheel aircraft (Turbulent) and it was undoubtedly very hard to land safely on tarmac with a tailskid but fairly easy with a tailwheel. The margins of error in making corrections before you're in groundloop territory are much greater with the wheel fitted. On grass though, a skid is definitely the way to go.
Perhaps your experience makes it hard for you to judge what's easy or hard for a relative newbie.