When to start from square#1?

I would say start from square #1, when you aren't prepared for square #2. Don't get ahead of yourself.
 
I suppose I should qualify where I'm at a bit, as 'frustrated' is probably the most accurate term. Don't get me wrong, I don't think I'm terrible, and I feel like I can lay a groovy beat and get some decent comping stuff cooking, but there is a stagnancy in my playing. Snare drum solos/etudes are particularly frustrating. I can physically play rolls and flams and the like, and use them in my own 'solos', but trying to play a piece that is written makes me feel green. I see lots of threads and videos on things like quintuplets, while I still struggle at effectively using duple-metered phases while playing a primarily triplet type rhythm, and vice versa.

Eh, none of that crap actually matters. Those last couple of things, anyway. Get playing with people and what matters will quickly become obvious. I suspect if you picked up a consistent, fairly serious practice habit you would make a lot of progress fast-- as long as you basically understand rhythm and there's nothing too screwed up happening with your playing. Find a teacher who knows what to do with Reed, maybe start hacking away at an intermediate snare drum book (Mitchell Peters's is good), you'll be fine.

Lots of awesome ostinato exercises (I actually think I have a sheet from maybe ToddBishop from years ago), but I can't convincingly play an ad-hoc melody over it that is musically interesting. 'Odd time signatures' get thrown around tons, but it sure feels like I'm missing the mark, as honestly sometimes I find myself struggling to keep my place in 7/8 or 5/4 without resorting to simple beats and annoyingly marking the 1's.

Simple beats and annoyingly marking the 1s is what most people want from you when playing odd meters, so it sounds like your golden, man.
 
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