Howdy fellow western mainer...
To me...it would boil down to a couple things,
A) How much heating are we talking? In other words, you just want to keep it at 40 or so thru winter and jack it up a bit when your there? Or you looking for 70 degrees 24-7?
B) How cold was it there this past winter?
In my new, very tight (for a garage, if I got rid of my garage doors it would be tighter then a lot of homes) it usually hovers at around 38-42 with no heat at all...R19 in walls, R38 Ceiling. It got as cold as 28 in there towards the end of Feb...so for me to keep it 40, should be no big deal. I would say if your in that ballpark and are looking to do the same, I would doubt that going to R30 would pay back in any meaningful way.
My Dad's 28x44 has R13 walls all the way up north, he keeps it 40 as well with no issue. It certainly wouldn't pay to rip it out and redo...if you were having to buy all new insulation for some other reason, then yeah I would say why not...but I think you could use your saved money for other efficiencies, and save more money. I.E. Changing your heat source from electric to whatever liquid fuel you want would be a bigger savings in my mind...BUT it all depends on what your looking to do.