for questions along the lines of "how many structural isomers does [insert organic compound here] have?" is there a way to ensure you don't miss any? like how are we supposed to think of the more difficult ones (e.g. methylcyclopropane for C4H8)
Yeah, I agree these sorts of questions are a bit daunting. You won't be asked about really large molecules with dozens of potential structural isomers, but in the example you gave C
4H
8 it is pretty obvious that it is not a straight-chain alkane or a straight-chain alkene. Therefore you can dispense with straight chain, then go straight to branched chain then maybe consider cyclo-compounds. The most difficult example you can expect to be asked is an oxy-compound like an alcohol, aldehyde or ketone.
Can you write out all the structural isomers of n-butanol?