Hi.
Quick question:
Is there any way to tell if I should “rendaku” a reading or not?
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Not really. In some cases, you can’t even be sure how to rendaku something. For instance, 奉 and 抱 both have the reading of ほう. And 信 and 辛 both have the reading of しん.
But 信奉 is しんぽう and 辛抱 is しんぼう
Maybe someone has come up with some rule that also has a ton of exceptions, but to me it just comes down to memorization.
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Alright, thanks!
I’ll just keep on memorizing these then 
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In short, no 100% rule. One may mistaken the Rendaku any time.
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As others have replied, no proper rules. That said, you will get a bit of a feel for it,basically you will use a rendaku when it feels more natural to say. It doesn’t work 100% (not even close to that) but you will start to get an ear for it and be able to guess when one will occur.
I agree with @musera. It took me a looooong time of studying regularly to start getting the hang of it, but I’m finally comfortable with it. Of course, there are still occasions where I’m wrong, but for the most part, I’m able to rendaku appropriately.
For me, just knowing that the word can be a possible rendaku word already helps a lot. If you don’t know what’s happening with the reading, you can get a little lost 
I’m not sure what you mean?
Sorry. What I meant is that a beginner might look at 人々 and completely get confused with what’s happening. “Why isn’t it ひとひと? ひとびと？Wth?”
Recognizing that rendaku exists is the first step. Then, I just try to think about the possible readings of a word, even if I know there’s only 1 correct. For example, 手紙 could have been てかみ or てがみ for all I know. However, by having both options in my mind, the real reading won’t sound strange to me at all because I already had it as an option. If I only gave 1 answer, I would be limiting my chances.
I do this with most vocab lessons and it tends to work very well. Not sure if I was clear enough this time
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I feel like 50% of my mistakes in reviews come from failing to rendaku something or not rendakuing when I should. :'D It takes so long for me to memorize how to rendaku!
For じん vs にん, the lose rule that helped me immensely is that anything that is permanent or impossible to change, such as ethnicity, age or country of birth uses じん, while non-permanent attributes such as occupation, or disposition, use にん. It’s probably not foulproof, but it’s good enough to help you distinguish them.
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