This is my take on the gears
I think the the amp is the most important thing in the chain. To me a good amp should have a wide freq response so u can hear the bass really deep to the sparkling highs. If you have a good guitar and pedal but a lousy amp then the amp will actually cut your freq and you lose all the tone your good guitar and pedals are meant to deliever. Another thing about amp is how loud can you push it before the sound start to distorted. The really small amps if you crank up the volume too much it will have cracking sound. For amps distortion I like it rich and heavy sounding. I use an Ibanez toneblaster TBX 65R I bought it during swee lee sales a few years ago for $275 up to this day I really enjoyed this amp. In my opinion it is better than Marshall AVT 100 watts, Marshall MG 100 watt. the Marshalls are very bright sounding amps which lacks the bass.
For effects pedal for distortion. I've tried many many pedals including, all of AMT lengend amp series, and a few other AMT distortion pedals, AMT SS 20 (which I own), all of the digitech distortions, Boss DS 1, metal core, metal zone, wampler triple wreck (which I own) wampler pinnacle, Seymore duncan twin tube mayhem, blackstar ht distX, blackstar HT blackfire (which I own), all the Beta alvin metal pedals, and I guess many others. Out of all these the AMT SS 20 really produce good sound for rhythm, very heavy and defined sound but it only will give that sound when u plug it into the return of the amp. The blackstar HT blackfire is impressive very defined sound even for the thick E string with distortion to the max it's still clear that pedal is more towards the warm side very good for lead playing. The wampler triple wreck is very thick sound I use that to "emulate"neck pickup sound because I do not have a neck pickup. The wampler pinnacle is quite impressive very defined and very crunchy stuff good for rhythm however the gain wasn't as high as my ibanez toneblaster amp so I didn't buy it. I'm thinking of getting the toneczar openhaus and/or the okko dominator.
I do own multi effects also like the Vox tonelab SE, boss gt 10, to me those individual pedals sounds much better, they have better freq response and much better clarity.
For guitar I would recommend you to get maybe something with 3 single coils, let's say you get another guitar with the same config with your current guitar, well the sound diff won't be that much i suppose because the price range is very narrow is like maybe 100 or 200 dollars more than your current guitar, so getting something with a totally diff sound that would be better so you can play more kinds of music.
Hope this helps