The question is whether you'll get $20K more enjoyment for the next $20K you spend on the new avionics. For some people yes, for others, no.
There are a couple more upgrades that would add value for me — new paint, a new interior, a modern audio panel, and a SIRS mag compass top the list — but replacing my steam gauges (which I like) with glass wouldn't make my plane fly any faster or better, and would take away a bit from my enjoyment, so no, not worth it (for me).
OTOH, I have no regrets about installing a simple autopilot in 2011, or an IFR GPS and ADS-B transponder in 2017—for me, they enhanced my flying experience enough to justify the money. But otherwise, I'd rather spend my next $20K on gas, recurrent training, nice hotels and meals for overnight trips, etc—it goes a long way there.