Players of Instruments, what are you having fun with lately?

I've played guitar for 34 years, so I can offer a bit of advice for a beginner. No matter what type of guitar you bought, do yourself a favor: take it to the nearest large music store and ask them how much for their guitar tech to do a setup on it. It's worth it for just about any guitar, and probably won't run you more than $60, depending on where you are. A setup entails getting the strings to their proper action (that's the height of the strings off the fretboard, and can make a very hard to play guitar much more playable).

Have the setup done with the string gauge of your choice--which in my opinion should be the lightest set you can find. You're a beginner, you have no calluses on your fingers, so a thin (light) set of strings will let you practice without getting overly frustrated by finger pain. Tone isn't important at this point, or at least not as important as the fact that you continue playing.

First things first: learn to tune the guitar, without a tuner. Use a cheap pitch pipe or pitch fork, or if you already have a tuner, tune the low-E and learn to tune the rest of the strings from there. Plenty of tutorials on youtube. You want to be able to do this because you won't always have a tuner; you might be playing someone else's guitar, or trying out guitar's in a store; but the bigger reason is, it's teaching you the relationship between note locations on adjacent strings. Very important, IMO.

Once you've got it down absolutely solid, and can strum a chord and hear which string is out of tune, you're a long ways to being a better guitarist, because nothing's worse than having your instrument out of tune, and guitars are notoriously easy to fall out of tune. Later, when you want a tuner, I recommend Snark. Cheap and extremely accurate; you can't go wrong.

Picks: picks or plectrums aren't usually given much weight, but they should be. They're the interface between your right hand and the guitar (unless you start out fingerpicking, which is a whole other ball of wax), and using the wrong pick can be discouraging. I play Fender Mediums, because they're absolutely legendary and have been used by everyone from bluegrass players to metal shredders. They have a "just right" kind of thickness that has become sort of a standard for all other picks. I recommend the line called "classic celluloid," because they use the older formula that you've heard on countless songs. Again, your choice, but for minimum frustration, give them a try.

If you need a capo, get a Shubb. There's no better capo out there. Ask anyone who plays bluegrass, where they use a lot of capos.

Beyond all that, I recommend simple song books. You're going to be a lot more satisfied a lot more quickly if you're making music instead of just "practicing" (even though that's exactly what you're doing by learning songs). It teaches you tempo and chord changes and a lot of the basics you're going to need to play the styles you like.

Good luck. It's a great hobby and well worth the investment in time and money--and none of what I've listed above is anywhere near "expensive" in terms of hobbies. Go make music.

Lenny is virtuoso-level work. I love SRV, and got to see him live several times, but Lenny is on another level from his other work. Testify comes close in difficulty, but not really. Lenny has lines in it that I steal just about every time I jam. I'd recommend taking it tiny piece by tiny piece, because that man is speaking a language with that guitar, and you wouldn't memorize a speech all at one go. Listen to a very short section that seems to be a phrase (it's easy with that song), learn it, learn it again, listen again for the nuances in his playing. Remember that SRV rakes the strings in almost everything he plays, and that adds a ton of character. His vibrato is almost impossible to duplicate accurately--hugely thick strings being wrangled by very strong hands is the only real way to do it, so work with what you have.

I'm not sure your level of playing, but Lenny might even be beyond that level at the moment. I've heard it covered a handful of times, and only one guy has done it any real justice. It's a really challenging song to cover well.

I feel like I'm at this weird stage where something I want to learn is either extremely difficult (Lenny, Another Brick in the Wall Pt. 2 solo), or possible to learn in 10 minutes (Everytime by Boy Pablo, Darling by Real Estate) with no middle ground. Any suggestions?

Again, I would need to know your level to suggest anything. Are you aware of Shutup & Play on youtube? He teaches you in a way that's very patient, very accurate, and allows you to learn pretty difficult stuff if you give it time, keep rewinding, and again, take it in small chunks.