I agree completely with you, Chili, as it would not seem to make much sense to invest upwards of 250 dlls Canadian in having a luthier refret any guitar that costs less than $1000.
But the alternate option also implies paying at least that much, with the only perceived benefit of becoming the proud owner of a set of fretting tools... which you can still use later and maybe even make some extra GAS money on the side.
So, IMHO it's a matter of deciding whether:
A) you place sentimental value over market value, damn the torpedoes,
B) the investment in tools represents a good opportunity to develop and hone a new and maybe profitable tech skill or,
C) you feel pragmatic and ferengi enough and decide to just forget about the refretting, sell the guitar to someone else and avoid the bigger "headache" while getting some liquidity.
And as Kuiil would say... "I have spoken".