If I discard 2+ cards, one being a land, another being a dredge card (Life from the Loam) while The Gitrog Monster is on my side, as long as I can dredge & have a land enter this way (and drawing via Gitrog), could I rediscard Loam & self mill indefinitely (assuming one of the 3 cards I dredge is a land)?
Your question sounds incomplete. The cards involved are any dredge card and gitrog, and I think you meant to have a card that allows you to discard a card such as Wild Mongrel.
If you have such a set up; when you dredge if you hit a land gitrog will trigger with this trigger on the stack you can discard your dredge card to the mongrel so it is available to be redreged. If you keep hitting lands you can churn through your entire deck.
If you didn't mean to have such a card and were asking if you are allowed to discard cards in your hand whenever you don't wake them then no, you can't just discard cards whenever you want.
At the end step, with cards that exceed maximum hand limit. Not just discarding without a cause.
Say I have 8 cards. I discard one because of cleanup (I discard a land). Gitrog says draws, but I dredge Loam instead, which sends another land to my bin, which draws me another card. Now, can I discard Loam & a land, causing Gitrog to allow me to repeat this (assuming I get a land to discard, and I dredge a land from Loam)?
If you discard Life from the Loam and a land card as your cleanup step begins and The Gitrog Monster's last ability triggers as a result, then after the current cleanup step, another cleanup step will happen when you will have to discard excess cards again (C.R. 514.3a, 514.1). If you discard Life from the Loam and a land card this way again, that ability will trigger again, so that another cleanup step will be added on. See also this thread, which involves Dakmor Salvage, a land card with dredge.
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If you have such a set up; when you dredge if you hit a land gitrog will trigger with this trigger on the stack you can discard your dredge card to the mongrel so it is available to be redreged. If you keep hitting lands you can churn through your entire deck.
If you didn't mean to have such a card and were asking if you are allowed to discard cards in your hand whenever you don't wake them then no, you can't just discard cards whenever you want.
At the end step, with cards that exceed maximum hand limit. Not just discarding without a cause.
Say I have 8 cards. I discard one because of cleanup (I discard a land). Gitrog says draws, but I dredge Loam instead, which sends another land to my bin, which draws me another card. Now, can I discard Loam & a land, causing Gitrog to allow me to repeat this (assuming I get a land to discard, and I dredge a land from Loam)?