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@benbrangwyn
Spokes don't stretch. Perhaps microscopically, but nothing that would require this frequent retruing.
Could be they're too loose and loosening off over time. If the rim is knackered and lots of metal worn off the sidewalls, that'll have an impact on wheel strength. The thickness of the wall at its thinnest point should be no less than .7mm on older school rims. You can measure it with a caliper or this wondrous tool which you can sometimes find on ebay as "watch caliper" for around a fiver - I use mine all the time checking rims. Fast, cheap, effective.
Re the earlier comment "bottom out on the thread" - that's a little misleading. A spoke nipple is usually 12mm long and the thread on a spoke is around 8 or 9mm. That means you can "bottom out" without any impact on wheel strength. However, if the spoke end is sticking up above the nipple any more than 1mm or mebbe 2mm (which can cause punctures on rims where the nipple holes aren't inset), then you're looking at spokes that are too long.
DoctorBike