Front brake

With hydraulic brakes there should be no "slack" As soon as the lever is squeezed the plunger on the master cylinder is actuated putting pressure in increasing amounts (as you pull the lever more) against the backside of the caliper pucks pushing outwards forcing the brake pads against the disc.

Cable actuated brakes could have "slack" in than as they went out of adjustment or the brake cable stretched.

I'm guessing either air still trapped or the master cylinder is going tits up.

The lever could be worn.

The bolt that the lever pivots on wears a oval shaped hole in the lever and the bolt can wear too.

Was anything done to the front brake? Did the bike tip over or anything?
Year of bike? Miles/KMs? ABS?
Sure sounds like air in the system as stated above. You say bleeding did not change anything, then the air is not get bleed out as air is being pulled back in...somewhere.
Could be at one of the caliper piston seals, bleed screws, M/C piston seal, banjo bolt crush washers, brake hose.

Sounds like you still have some air in the lines. If you end up doing another bleed, also consider swapping to braided steel hoses. This really improved the spongy feeling on mine. I made the swap at 40k miles.

Will the brakes pump up ?

If yes air is the most likely cause.

If no a mechanical issue is more likely.

I am starting to wonder if it's time for new lines too. I have a 2009 Wee, stock hoses. Lately the front brake is fairly squishy, it won't pump up like it would if it needed bleeding, so I'm wondering about the hoses softening.
Is that a thing? If so, any recommendations on a hose kit?
Thanks

I'd suggest that you also install speed bleeders while you're at it. Probably my favorite upgrade lol. Also, if you just put a new lever on, a little filework might be necessary, my new 'oem' lever was a tiny bit too thick and binded just enough for everything to feel off.

@shawnsjam, what year and model V-Strom do you have and what is the milage?