Roloccolor, the following answers came from the FAQ section of the Winstep.net website:
"Q) What is the upgrade policy for Nexus Ultimate and Winstep Xtreme?
A) Essentially you get free upgrades for one year after purchase, and after that, whenever you want, you can get another year of free upgrades for a fraction of the original purchase price. You should find all you'll ever need to know about Winstep Xtreme's upgrade policy here and about Nexus Ultimate upgrade policy here.
Q) Why don't you offer free life time upgrades when I purchase your software?
A) How long do you think a shop would manage to stay in business if it had to rely solely on a constant stream of new customers? A large slice of every successful company's income comes from repeated business. This actually benefits YOU too: unhappy customers are unlikely to come back, so naturally we want to keep you happy! Feel free to read this article here to find out more.
Q) Ah, but the Winstep Start Menu Organizer Pro comes with free updates for life!
A) Yes, but only because that is not the type of application that we need to upgrade constantly. It does a relatively simple job, and does it well from the very beginning.
There's a lot more there, I just limited what I cut and pasted because of your question, and the desire not to copy and paste a wall of text.