That all sounds familiar to me.
Substitute Joe Strummer and Keith Richards in my case, so I got a Telecaster.
Sore fingers after starting to play again after thirty years, yep.
Browsing more expensive guitars on-line, that I will never be able to justify, yep.
Vox AC30 headphone amp to go with my new guitar yep.
By the way the iRig which has already been mentioned is also good, connects your guitar to smartphone/tablet/PC/Mac where there are lots of apps for different amps, pedals and other effects, much bigger choice than the AC30 device, also has a headphone output. You could probably find an app with that Marshall stack you mentioned.
https://www.ikmultimedia.com/products/irighd2/