It literally means ‘head of an association/society’. If the organisation is called ‘[something] 会’ for whatever reason, then 会長 makes perfect sense as the title for the boss/chief.
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散策 - walking; strolling
Jisho lists it as a common word, but it’s not in WK or the Core10k 
(but the similar 散歩 obv is)
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Huh, perhaps it’s because you’re more likely to say/hear 散歩 since that’s how you can say you like walking, but 散策 seems to be more like “walk on the left” kind of walking?
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The two words have each other in their definitions.
It seems that 散歩 is more likely to be used when walking around where you live. 散策 is more likely to be used when walking and sightseeing are going hand in hand.
Additionally, animals do not 散策する apparently, whereas they can 散歩する, and you often hear that with dogs.
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相好を崩す - to smile broadly; to grin widely (Literally “demolish one’s face/appearance/features”)
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血豆 - blister 
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クリパ - Christmas party
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自発性 じはつせい spontaneity
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登場 - entrance (of a character in a play or movie or game) or introduction of something into a market
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I’m not sure if this is clear from the kanji, but this is fairly literally ‘stepping up (登) into a space/place (場)’, with that space being the one reserved for the activity being discussed, like a stage. I think deducing its other meanings from that is relatively easy.
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Tentacle is 触手 certainly a critically important word in Japan.
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Certainly, when we’re talking about タコ ;).
坊っちゃん - young master (also a book by 夏目漱石)
I initially thought it’s a more casual version of 坊さん, but alas.
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I suspect the two are linked since there’s also 坊主 can also mean ‘boy’ even though its main meaning is ‘monk’. Maybe such word developed out of the prevalence of Buddhism in Japan.
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There’s also 坊や, btw 
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If I’m not mistaken, the etymology goes something like:
坊 was a division used within a city in China, and subsequently also in Japan.
It then came to refer to a small temple within a larger complex, the master of which was a 坊主. This development was unique to Japan, which is presumably why the hanzi 坊 has no strong connection to monks or temples in Chinese.
The connection to boy may have come about because the person in charge of one of these small temples was normally a young man, and possibly also because monks are very fastidious about shaving their heads, making their heads clean and shiny like that of a young boy.
Edit: Some sources:
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From The Complete Guide to Japanese Kanji by Seely and Henshall:
Shirakawa notes that 坊 was used to denote plots of land - typically square - in a city divided up in terms of a traditional grid system. In turn, 坊 came to be applied in a Buddhist context for the divisions of space in a temple (including rooms), and the chief priest was known as 坊主, a term which later came to be used as a general word meaning ‘(Buddhist) priest’; ‘boy’ seems to be a generalized sense deriving from ‘young boy priest’.
Edit 2:
For the sake of being on topic:
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滴 - てき - counter for drops (of fluid)
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一滴 - いってき - one drop, an individual drop
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This word that at first glance looks like a verb, but is actually an adverb:
- 頗る - extremely; very much
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This is more of an expression but I found it under a Japanese YouTube video and didn’t really know what it meant at first:
神すぎる
At first glance it looks like: “Surpassing God”; turns out its used when something is very good or you like/enjoy something very much, or when something is 「すごい」. Apparently frequently used with anime/manga stuff.
The reason this works is that 神 is used as an informal adjective/prefix e.g. 神アニメ=‘a godly anime’ i.e. an amazing anime. As such, just like a typical adjective, it’s possible to attach すぎる to the stem to mean ‘too [adjective]’.
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I see, thanks for the explanation!
A while back I posted a metaphor (灯台下暗し - it’s darkest under a lamp post), but without a follow-up which I should’ve researched a bit:
街灯 - street light (very literal)
街路灯 - street light, but uses the 路 kanji to maybe emphasize the “next to the road” aspect of it