The best guitar is the one you feel the most comfortable playing. You can improve electronics if they're lacking. Being comfortable though? Irreplaceable. Your most effortless performance will have effortless tone... everything electronic is just a potential bottleneck to be overcome. In my experience less is more. The shortest path from strings to speaker is best unless your sound us more about special fx than playing and that's a thing too, but otherwise? Be comfortable and if you like your pickups etc don't bog your signal down. More of your personality will reach the speaker.
In amps I think simple is best. The more features you want the more you need to spend in order to get quality implementation. A simple circuit that's well voiced using high quality components always kicks butt, which is why the vintage amp market is so inflated. Modeling stuff improves every year though and I no longer sneer at it. Don't discount a direct solution these days.
EDIT: personally I usually play an SG standard into something with dirt, either fuzz or OD or whatnot (usually turned off) into an ep3 that drives my cranked 62 ac30 or this amp I built on the bones of a 60s traynor PA I named the "jimwatt"and I use my volume control a lot these days... I add other stuff as necessary when recording, but keep it relatively simple. My other rig lately is a tele into an early 60s Ampeg Mercury 1x12 combo, straight in. It's filled the role of the tweeds and supros I've had and I think I prefer it. I've been through a lot of small combos, mostly winners for 1 or 2 styles but this one is the most versatile if you don't want spring reverb... It can really do whatever, from tweed deluxe to zep1 and even into cranked low wattage marshall tones. Just don't try metal. The tweed super/pro are also great amps... same amp with different transformers and speakers. If you play gibsons try a super, if you play telecaster try and pro.... for a strat check out the tweed 5e3 bandmaster or just go blonde or blackface :-)
sleeper vintage gems I recommend:
Ampeg: jet, reverb-o-rocket, mercury, early gemini1s, b25/b25b (difference is grounding, b25b is saferwith modern outlets). Drawback to the b25 is the rare 7199 pentode/triode driver/phase inverter tube but it can be converted to a 6 an8 with a simple pin-out swap if I recall.
leatherette, 2 tone and tweed gibson amps: GA20, GA30, GA77, GA14 titan, GA6 lancer, GA?? ranger (some mods to the pentode channel will up the ante)
Airline amps: 9023A (supro 1624T), 9320A (supro thunderbolt)
Danelectro amps: Dan-O DM25, Silvertone 1483 (not just for bass, kills the 1484 jack white digs)
Garnet amps, all of em
Laney: AOR heads are all pretty cool, GH50L, GH100L (jcm800s on crack, new models arent built as well, go 80s or 90s)
Musicman, anything 70s... most are solid state preamps with tube power amps. Leo Fender's ultimate clean designs. Indestructible. Good enough for Joan Jet.
Naylor: dual 60, not exactly vintage but pretty cool and not well known. Joe Naylor went on to found reverend giitars.
Oahu: if it's got a palm tree on the grill cloth it secretly wants to rock. Turn to 10 for best results.
Peavey: VTM120 (a jcm800 clone)
Selmer: treble n bass heads, mk3 is the best deal, mk1 and 2 have better tone for most folks, all are fine and 3s can be modded into 2s if you care
Plush: anything, they're all fender and marshall clones in Kustom clothing
Sunn: 200S, Sorado, Sonara, Sorado, Scepter... basically the same heads with small voicing tweaks or different on-board fx, they're built on a 60s dynaco hifi kit with a fender inspired preamp instead of consumer line in. The transformers are TOP NOTCH. Same drawback as b25 on most models.
Traynor: YGM4 studiomate (like a marshall 20w Treble N Bass head but in 4x8 combo), YRM1 reverbmaster (good stock, moddable to a fender twin in a head), YVM1 voicemaster PA head (ok stock, dark and growly, easily modded to rip)... the old hammond transformers on these kill it
Univox: all their tube heads are pretty tasty. Inferior components to a lot of their competition but still good. Excellent build quality, easy to service and modify.
Vox: V15, V125 (the Heart sound... loud loud LOUD)
Yamaha T100, T50C soldano designed tube amps... G100, G50 are solid state clean machines great for pedal guys and fans of 80s new wave and post punk tones, cleaner than a jazz chorus and cheaper too