I too feel that getting a few pedals may be the best way for you to keep your basic tone while expanding the sounds you work with.
I was in a similar position a couple of years ago, and decided to go the pedal route, culminating in this rig:
It's by no means a particularly complete or boutique set-up, but it does what I need it to.
The pedals I truly rely on, especially when playing through a non-MV single-channel tube/valve amp like my Velocette/Gibson GA15, are the compressor and the overdrive. I could easily gig through 90% of our set list with nothing else but a guitar and cable (we play blues, '60s/'70s rock and pop, Dire Straits, Pink Floyd, ...).
The latter led me to get a delay for Gilmorish solo forays, and also provides looping capabilities (which I seldom use). Adding Police songs to the list warranted getting an old-school chorus pedal. The wah is for Cream, Clapton, Hendrix and just general messing around (still fun after all these years!). The Fuzz Factory is for when you want to experiment with gnarly sounds and sonically get in people's faces... Finally, the Turbo Tuner is set up to kill the signal when engaged so that no one hears the tuning process but me.
The beauty of this approach is that you can keep it simple and modular, adding what you need when you need it, and keep it analogue if you wish (the delay/looper and tuner are the only digital pedals on my board). Im not suggesting that digital doesn't get close, but I'm old-school and value the simplicity and (to my ears) more organic character and sound from analogue pedals.
More importantly, you can really fine-tune your choices by trying out a number of options for each pedal type before settling on the one that sounds best to you.
Having said that, I still find myself playing straight into my tube amps when we can play at higher volume, because it's just plain fun...!
Good luck with your search. The journey's at least as much fun as finally getting it all put together.