Re: Your first good guitar - do you tend to stick to ones similar to it?
I know this sounds crazy, but only because I've bought, sold, and traded a lot of guitars, but I've had around 80-90 guitars. One thing I've learned is that your ears and hands get used to anything you play for a few weeks, but you gravitate toward a few favorite styles. My first "good" guitar was a 84 Carvin DC400/Red/ebony board/Kahler trem. Since it was a stratshaped Gibson type guitar, it allowed me to be comfortable on both neck thru's and bolt ons. I learned how to play in my teens on that guitar, but it has been long gone since 1989.
Based on your style and preferences, Nuntius, I think you should get a strat shaped body w/neck thru or bolt on, 2 hums, and a 3 way toggle. Floyd or blocked down Fender type trem. As for pickups, many guys tend to go for the heavy metal pickups, but you should look into the more toneful ones. On singing highgain, they tend to produce better tone than most younger guys would think. I've been doing a bunch of highgain "shred" playing recently, mostly due to this forum's influence, and a return to what got me playing guitar. The Seth Lover neck sustains beautifully, and really sounds articulate for sweeps. I always thought that pickup would excel for just blues, but it sounds great for the type of stuff you and Diminished D play. I started as a technical rock/metal guy, then spent the 90's doing blues/bluesrock, then the next few years returning to songoriented modern rock. I'm finding that the best Duncans sound great enough to use for ANY style of music....just different amps.