Same way you decide everything
You look at the abilities of your party, and look at the abilities of the enemy, then work out your best option.
This may sound flippant, but even if one option was great in a lot of circumstances, there are enough different enemies in D&D, and disadvantage on checks is so situational, that it is quite possible you could never use it meaningfully if you just played the percentages.
To help you make your decisions there are a few things you can be aware of:
What ability checks does your party force upon the enemy?
There are way too many combinations that could reasonably be listed here, but if you list the members of your party we might be able to provide a more meaningful answer. The best advice I can give is to speak to your party members (in or out of character) and learn what they do. This works for far more things than just hex, and is always an intelligent thing.
What ability checks is your party vulnerable to?
Giving disadvantage on str checks which are likely to be performed against your raging STR 20 barbarian is an option, but not necessarily a useful one. If your 'tank' doesn't have any proficiency in athletics or acrobatics, then that changes. Again to find this out you need to speak to your party and understand what their characters are good or bad at.
What ability checks do you expect the enemy to try and force upon your party?
This is difficult without metagaming and knowing the enemies, but your DM will hopefully be able to help with the way they describe the enemies. Writhing appendages with no stingers or weapons can indicate an incoming grapple, spears on chains similarly. Skulking characters in the shadows that you only just notice because of your passive perception can indicate a rogue likely to try and sneak up on you, equally your party rogue might want help hiding by debuffing the wisdom check of something that sounds clerical or druidic.
If your DM doesn't give you good descriptions of the enemies you are facing then this becomes harder, so speak to your DM.
What ability checks should I be concerned about?
This is a last but not least mention, certain checks are more likely than others, and some have hardly any combat implications. It is very rare for an enemy to use a history check to do your party any harm!
Options:
- STR: Initiating grapple checks; athletics to escape grapples and some spell effects
- DEX: Stealth checks; acrobatics to escape grapples
- CON: Exhaustion?
- INT: Potential interactions with your illusions; checks for counterspell and dispel magic
- WIS: Perception, breaking free from certain fear effects (wrathful smite, but that imposes disadvantage by itself so this likely isn't needed from you); checks for counterspell and dispel magic
- CHA: Talking, but useful for when you intend to capture and interrogate rather than kill, but technically that is an out of combat use; checks for counterspell and dispel magic
Summary
You are far more likely to get mileage out of helping an ally impose some kind of effect rather than using it to avoid some kind of effect unless you happen to have very specific knowledge about what you are fighting. Speak to your party and ask them what would be useful!