You are right, it's a lot of considerations.
Usually I have my entry target price, which in most cases I specify in the discussion topic. Then I might place limit orders on several strikes and wait. Sometimes "playing" with the order helps - meaning cancelling the order and resubmitting it, changing 1-2 cents back and forward etc. Scaling in and out of positions helps as well.
Getting good fills is a process. It takes time to master, and nothing substitutes experience. I wasn't born with it, it took years of experience and hard work.
Some instruments are more difficult to trade than others, and when liquidity and fills are an issue, I don't trade it.