Yes and no.
Yes, on this level one never knows what he might be missing unless he tries out new things.
No, if your not trying to own and have a collection of guitars.
I played bass for years and stopped for years many years. Anyway I kept my Peavey T-40 from 1979 it was my 1st real bass. I was always pleased with the sound and feel of that bass. Forward to 2007 I wanted to start playing again went out shopping for a new bass tried a whole lot of the usual suspects, Fender,Music Man, Washburn, Warwick, Jackson, Peavey, Pedula, Modulus, Lakland, etc. etc.
But once I laid my hands on a Ibanez SR500 the search was over it was if they custom made that bass for me perfect fit for my hands and the sound & tones are endless. I found the ONE as some say but with that said, I do want 2 Ibanez prestige series SR Basses (bolt on & neck-thru) and once I do I'll be set for life or at least at this moment that is the statement I'll stand by. LOL
As far as Guitars go the middle of December will mark the 1st anniversary of my journey into the world of guitar playing. I 1st bought MIK telecaster double HB coil split very flat neck 15" very nice guitar but I knew I was going to want a Stratocaster one day I now have 2, each one sounds different and feels different but I love them both and plan to keep them a life time.
I now know because I have played a while and I still stink at it mind you

. I do know for certain the sound I want or have in my head I know what guitar to use to get it and what guitar I want to buy because I can come close to it but not capture it exactly. So, Now I have a short guitar "GAS LIST" (a phrase I learned here, Thanks guys!).
A real tele 1 with noiseless pickups and 1 with out. 9.5" C or soft V for rock & blues.
A strat with rosewood fret board with noiseless pups. 9.5" C or soft V for rock, funk, and blues.
A LP style Guitar Micheal Kelly has 2 I want badly (one with direct mounted pups and the other with EMG 85/81 pups). MK its the cheaper way to go to for the LP sound I want. One day I hope to own a Gibson LP, Heritage, & Collings LP's style axes (I learned about Heritage & Collings here as well) for rock, metal, blues, & jazz.
There are just certain sounds that each Guitar brings to the table and since I want to have those sounds available I will have a small collection of guitars for sure in no time and only a few basses all Ibanez SR series.
So, I say go check out whats out there never know what you might find and fall in love with and have to it.