Grammar is often a frustration to the writer but it doesn't need to be. Both the frustration and the help that can come from grammar exist for the same reason. Unlike almost any other part of the writing process there are set rules for grammar. You will learn these rules as you write more but the faster you learn them the better off you will be.
One of the most straight forward of these rules is the use of contractions and possessives. And though there are a couple judgment calls on when to use contractions the rules of how they were are really pretty simple and knowing if they are right isn't difficult.
Starting with possessives the question is of ownership and plurality. Typically, you will be using a possessive when referring to something that someone owns. Tom's Car and this isn't all that difficult. Use and apostrophe and an s and you've got it. Where this becomes a bit more difficult is when you have the name James. You can't write Jame's because that's implying that his name is Jame, but writing James's doesn't look very good and so instead you put James' though this is more of a judgment call than Tom's car and you probably won't be called out to often for James's.
To make this even more confusing you can add to the mix something that is owned by multiple people. Again the difficulty isn't too bad when using something that doesn't end with s. Men's cars is basically straight forward. But what about cousins. This is especially confusing because if you get it wrong you can change the number of cousins you're talking about. Cousin's cars would refer to a single cousin with multiple cars while cousins' cars would referee to several cousins each with at least one car. So long as you are careful though it shouldn't be a major problem.
The other use of apostrophes is even easier to ensure is correct. That is the use of contractions. First though you must decide if you want to use them at all. Using a contraction is a sign of informal writing and while they have become common in most forms of writing it is still worth considering. A truly formal letter is well worth writing without contractions.
If you decide that you do want to use them then the key to using them correctly is to never read them in your mind as a contraction. This may seem odd but once you get use to it things get easier. You're and your are the easiest example. If you simply read you're as you are every time then you aren't likely to misuse it because you're unlikely to read you are car rather than your car and think it is correct. This habit will work for nearly all contractions.
These may seem like minor points of grammar but largely that is the point. Apostrophes are not difficult to get correct so why make yourself look lazy to someone who might otherwise like your writing. Grammar is one of the few true rules of writing so hold onto it and be glad that there is firm ground somewhere.
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