I believe, if you buy Start10 now, it is yours for life. Just that you will entitle for any upgrade within the same version number. So now Start10 is at 1.7. so you are entitle for free upgrade within that version number. 1.x. But if Start10 goes to v2.x or anyting above that, you will need to pay for that version usually at a discount since you own v1.x.
Different story if you subscribe to Object Desktop that come with Start10 and other softwares at a every low price. That is yearly subscription base. Where the subscriber enjoy free upgrade for all the listed software once it get an update as long as the subscription is active. More on it here : https://www.stardock.com/products/odnt/
Let us know if you still need our assistance.
Thank you,
Basj,
Stardock Community Assistant