[Someone1234]

Maybe I misunderstand, but my experience is that purchasing a normal vanilla domain name is very easy and very user friendly. The only common issue I have seen is annoying upsell (e.g. "we've dropped an $99 SSL package into your basket, remove it if you don't want it!").

Buying already occupied domains is always a huge hassle. No two ways about it, and a lot of the sites which sell/resell them are scummy as heck. I try and stay away from that as a general rule.

[modzilla]

I guess my question did not emphasize the "non-standard" enough. I have purchased many domain names that fall in the $10~$20/year price range without any problem.

I am most curious about complex domain name purchases and the experiences people have had - things that work and things that have not worked.