I'm just curious, in my lease it says that my landlord will collect the rent of the first of every month, well it's nearly halfway through January and he still hasn't come to get it. Is it my job to go to him and say here's the rent, or can I just wait for him? (I've had to chase him down every month to pay, he's never once come to me to get it.) Does it work like monopoly, like if he doesn't ask for the rent by the end of the month is he SOL (you know how in monopoly if someone lands on your property and you don't notice they don't have to pay the rent once their turn is over)? I'm going to pay either way, it's just something I've been wondering about.

No, if he does not come and collect the rent it is not like Monopoly and he is SOL. You rent from him and you owe rent the first of each month. If he lives in the same town/city as you, you can mail him the rent check on the 30th of the month so he gets it the first. That would eliminate chasing him down. Have you called him and talked this over? He must have the expectation that he will be paid.

What does your lease specify regarding payment of the rent? Generally you would just mail it in when due, much like any other regular payment. But if your lease stipulates that he is to come and personally collect it from you then just wait until he comes for it. Of course, such a "hit-and-miss" approach can be a pain in the neck when it comes to keeping your records and balancing your checkbook. If that's a problem for you then ask your landlord to either allow you to mail your payments or ask that he come by at the same time every month.

No I'm renting a room in his house, so literally he could walk down the stairs and come get it, but he doesn't. I'm still going to pay, I just wondered how it would work if he never came to get it. Too bad life isn't like monopoly.

You rent a room in his house. Why can't you walk up the steps and hand him the rent check? Or put the rent check in an envelope and put that in a visible place for him to see? The burden is not all his. Or mail it to him? He has to check his mail. If the two of you are that uncommunicative about collecting the rent - what do you do if you need something repaired?

If he does not come up after I and you don't pay, he can just evict you or change you late fees.

I paid it yesterday, I'm really busy and my schedule isn't in sync with his for when he'll be home so I usually forget when to pay, or if I have actually paid it for that month before, or what. I think I'll put it in a place where he can see it, that's a better idea.

I think you need to get a daytimmer and keep your pay scheudle, maybe ever a written budget. And start to remember if and when you pay.
Sorry but paying rent is one of those more serious things not to forget items. Also it should be a place you both agree to put it, he has to know that is what you are going to do.

It appears this is an amicable relationship, at least for the present. Does the lease actually say the landlord will collect the rent on the 1st or does it just say the rent is due on the 1st? If it specifies that he will collect then it is his responsibility. So it can't charge you late charges or evict you if you don't hand it over on time. However, if it just says its due on the 1st, then its your responsibility to pay it. Doesn't the house have a mailbox? If so, just leave in the box.