I'd like to sell a 2018 version of my app (1st release) for a set price, provide minor updates throughout the year for free, and then put out a whole new App (major upgrade) in 2019 for another set price in like fashion, and annually thereafter. Can I do this? Or does this have to be done via In-app purchase (non-renewing prescription)?
Business model question
A 'whole new app' would mean two unique apps, especially if you remove features that users have already paid for, which is not allowed.
If you're talking about recurring/annual fees for content/services consumed in the app, tho, then yes, IAP - see: https://developer.apple.com/app-store/subscriptions/ - and the ASRGs Business section.
Once a user purchases an app they get all future versions for free. You can either create new apps each year (not new versions) or upgrade the app with yearly IAPs.