I am constantly working on memorizing standards and have been for years. I follow the same pattern every time I do it, which I learned from my teachers who had been doing it the same way for years. I don't know how many gajillion times Ive done it now over the last probably 20 years or so.
I learn the head first. Like the OP, I do like having a recording of it to play over, because often you are having to try to figure out a fingering that lets you get decent phrasing, which can be a lengthy process, particularly on the upright. There are some heads which are sufficiently difficult that I abandon the effort in the interest of time, if I need to have the tune together for a gig, but often times I come back to those later to see if I can figure it out. It is well worth it not just because it helps you to hear the changes in your head, but also because once you get the melody burned into your brain its helps you not to get lost in the form, particularly if there is trading going on, you can just hum the melody to yourself instead of counting.
Many recordings of standards have the heads played with enough embellishment that they can be difficult to use as a reference, so if I can't find something I can work with, ill sequence it, or find somebody else's Musescore transcription and use that. It doesn't really matter if the sequenced part swings or not, since I am only going to use it long enough to get it memorized, subsequently I'll just play over a backing track or a metronome.
Once I have the head together, or have abandoned the effort, I usually pick a couple of choruses and transcribe those. I don't always do the notation, unless its some part that is just so ridiculously good that I'd like to have it for reference, or the guy I study harmony with will ask me if I have a piece I want to look at, I can draw from those transcriptions. Regardless of whether I write it down, the goal is just to memorize those couple of choruses until I can play them by heart.
Once I get my two favorite choruses down, I can usually play the tune on a gig, but it takes a few weeks of replaying that section a couple of times per day before its really committed to memory, and even then sometimes if I play it on a gig, the transcribed part completely disappears from my memory, and I fall back to just hearing the changes in my head and improvising until some of the stuff I absorbed starts bubbling up from memory.
In general I won't ask for solos unless its on tunes that I know I have something to say on, but after I get the line down I will definitely devote several hours to soloing over a backing track, in particular, soloing over particular changes in the chart until I feel like I can hear them really well. If I have Aebersolds for it, it's well worth studying the recorded player's lines (I love Tyrone Wheelers stuff in addition to R.C.) over those little two bar sections, as they hear so much hipper stuff than I do, and I have learned a tremendous amount of sounds that way that I would never have come up with on my own. But its good to have some kind of concept of what you might play if called to take a solo, so its worth fooling around with it. Often the first few dopey ideas I come up with wind up sticking in my head and I later use them.
But anyway, yes you should learn the head in my opinion, but I wouldn't sweat the technical details of how you get the accompaniment for it; just use that as a crutch to get you to where you can play the head from memory, get the fingering together, and then move on.
