Signing on Windows is a pain in the arse and gets more expensive every year. I dread having to renew my certificate. Also they keep reducing the maximum certificate length, so you can't just do it once every 5 years, like you used to be able to.
I can't remember how difficult it was to set up my initial Apple developer account (trauma related memory loss, perhaps) but it is dead simple to renew. Just pay the $99. I did it yesterday. Took about a minute.