Is there a way for a martial character to flank on their turn, flank on an allied martial's turn, but not be within reach of the enemy on said enemy's turn?
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Yes. Flanking with more reach than the enemy has. Or Spending two of your actions to Ready to step away after your ally attacks (if you aren't readying something like Skirmish Strike, you may not want to spend your actions that way, but it's an option).
I would look for feats and abilities and spells that let you cause an ally to move on your turn (like courageous advance for the bard).
Also, there is also shove and various effects that do similar things to shove.
Being a Goblin can possibly help it if a Step is sufficient. At least our Goblin Rogue got good use out of it while being low level (=not this much opponents with reach).
Being a Goblin can possibly help it if a Step is sufficient. At least our Goblin Rogue got good use out of it while being low level (=not this much opponents with reach).
Even better with a tiger Monk goblin.
This is why I often prefer other methods of applying flat-footed. A tripper or alchemist really improve a group going for a hit-and-run strategy.