#1
2001 Fender MIM Fat Strat
Epiphone Valve Junior Combo Amp

Boss DS-1 Distortion Pedal
#4
The amp and guitar? Fine.
The pedal... not so much.

For blues you want overdrive, not distortion. I believe Boss do an overdrive pedal specifically meant for blues, the BD series I think. Though failing that, Digitech have the Bad Monkey and Screamin' Blues pedals, both of which are superb (Bad Monkey is lighter and is made to give you a specifically overdriven tube style of overdrive, this it will effect your tone slightly; the Screamin' Blues is actually, despite the name, more of just a general all-round overdrive and distortion pedal and can even get up to near metal-like qualities, and doesn't effect your tone as much though it does mean if you were to ever use it with worse gear, it can sound pretty poor).
#5
Try an Ibanez Tube Screamer pedal. It gives you a real beefy pushy overdrive sound.
BOOM-SHAKALAKALAKA-BOOM-SHAKALAKUNGA
#7
Yeah, you can sell it...

It's not an awful pedal or anything, just far too fuzzy and modern for blues and most rock. Maybe you could trade or part-ex it for a TubeScreamer - type pedal?