The issue is not 'loss of signal strength', but 'pick-up of interference'.
The 'pre-made' cords at Radio Shack, etc. are usually what is called 'satin' cord. Notably, all the conductors are laid out exactly parallel in the flat cord (same arrangement as 'ribbon' cable', just with a small number of conductors.)
Such 'flat cable' is much more prone to pick up interference, etc, than is a 'twisted pair' cable.
In twisted-pair cable, the position of the individual conductors changes 'frequently' (depending on the 'category' of cable, it may be centimeters to 10s of inches). This results in the different sections of the cable picking up the interference *differently*, and the signal pick-up in the different sections effectively cancel each other out -- with just the 'intended' signal going through. It isn't "perfect", but it is much *much* better than what happens with 'flat' cable.
Note: Radio Shack, etc., also sells 'spools' (50', 100', maybe 250' and longer) of 'round' telephone cable -- which _is_ 'twisted pair' construction. You can easily build-you-own long extension from that.
The authoritative answer for that is "whatever works". *grin*
Seriously, the phone cord _itself_ is a 'non issue'. It is "what else" that is in the vicinity, *generating* interference, that is the primary problem.
There are *no* _official_ "rules" limiting length of extension cords
-- and you can always buy a 'coupler' (sold at Radio Shack, etc.), to join 2 25' extensions, giving you a 50' reach, for example.
Probably the primary reason you don't see cords longer than 25' for sale is that there would be a _very_small_ market for them. 10' and
15' cords out-sell the 25' ones by a *big* margin -- something like 25:1. I'd expect _at_least_ 10:1 to 15:1 for 25' vs 50'.