I'm thinking it shouldn't be too difficult to support upgrades from now ("R") until the next LTS (let's call it "S"), since Ubuntu already supports upgrading from one LTS to the next. Once the next LTS is released, you'll have to upgrade to the LTS stack first then you can hop back on the daily or monthly train ("T"). This allows that T train to drop the migration code for upgrades to S.
Although if you've gone a year or so without upgrading, then maybe you should just stay on the LTS.