Shunshoku Umegoyomi Vol. 1: The Tea Caddy Zangetsu

Returning after a (long) break:

Fig. 1: 二番
ばん頭久八
といふ者が
信切に。お
れが名代に。
畠山さまへ
行たれバ。

"When the second clerk, a person named Kyūhachi, kindly arrived at Lord Hatakeyama['s residence] as my representative (fig. 1), he [Lord Hatakeyama] immediately agreed to give me the money, but the other day he had commanded Matsubei (fig. 2) to take a tea caddy, Zangetsu, to sell off, and when he asked [about it] at this time, [he learned] it had been sold to the Kajiwara family for 1500 ryou (fig. 3)."

Fig. 2:
随分金子
ハ下げつ
ゝハそが。
先達て待
兵へにお
ふせつけ
られた。

First of all, note the irregular kanji for 「親切」 (meaning "kindness"). The first character written with the kanji 「信」 instead. Since I can't decipher any semantic connection between the two kanji ("faith" for 「信」 and "parent" for 「親」), it appears that this is purely due their homophonicity (both can be read as 「しん」).

Next, note the use of the particle 「が」 (after 「おれ」) to indicate possession, analogous to modern Japanese's 「の」.

The sequence 「行たれば」 can be broken down as the verb 「行（い）たる」 (an irregular writing of the verb 「至（いた）る」) in the realis form （已然形）, followed by the auxiliary verb 「ば」, which here takes on the temporal meaning of "when".

Moving on to fig. 2, I had difficulty parsing 「下げつゝハそ」. I think that 「下げ」 is derived from the classical verb 「下ぐ」. However, after searching through the various entries listed on that page, I couldn't find one that really fit this sentence. My best guess, based on the context, is that it takes on the opposite meaning of 「上げる」 - that is, "give (to someone below you)", similar to 「遣る」 in modern Japanese.

Fig. 3:
残月の
而茶入。
而拂もの
とてわた
しおかれ
しが。此
ほど聞バ
梶原家へ
千五百両
納りしと
の事

I had no idea how to parse 「つつハそ」. 「つつ」 in classical Japanese takes on a meaning similar to 「何度も」 in the modern language - it indicates repetition. But that by itself wasn't too helpful.

Edit: as Chris has suggested in the comments, 「つつハそが」 might be interpreted as 「つつ（こと）ハそ（れ）が」, where the kana in parentheses are implied. The meaning/translation would basically stay the same.

Finally, the verb 「おふせつけられた」 has the same meaning as the MJ 「おおせつける」, or 「仰せ付ける」 - “to command/request/appoint”. The difference is in the kana. The MJ noun 「仰せ」 comes from the 古文 verb 「おふす」, or 「仰す」, also meaning “to command/appoint.”

In fig. 3, we see the word 「残月」, which I had difficulty figuring out the meaning of. It appears to be just the name of the tea caddy （「而茶入」）, but it would be great to get some clarification on this matter. One minor detail about the furigana - note how the dakuten are missing for the 「ざ」, but not for the 「げ」.

Fig. 4:
夏井丹次
郎よりさし
あげ至たる
五百両を
さし引遺り
千両は。
早速に上納
いたせと。
いはれて
びつくり
立かへり。

「梶原」, on the other hand, is clearly a family name, which is particularly clarified by the use of the kanji 「家」 right after it. It would be read as 「かじわら」.

「而拂もの」 is similar to the MJ 「払い物」, meaning "discarded article".

「此ほど」, read as 「このほど」, means "at this time".

The final point to note in fig. 3 is the irregular use of the kanji 「納」 for the verb 「収まる」. It is in the continuative form （連用形） and followed by 「し」, which is the auxiliary verb 「き」 (indicating personal past) in the attributive form （連体形）. The attributive form is necessary here because it is followed by the particle 「と」.

"Kyūhachi was told that, deducting the 500 ryou to give to Natsui Tanjirou, the remaining 1000 ryou must be immediately repaid, and so [Kyūhachi] returned in shock (fig. 4)."

In fig. 4, I wasn't sure about the kanji in 「至たる」, so if that's wrong, let me know.

Edit: Chris has suggested below that it might be 「老たる」, but I can't find a matching dictionary entry.

The compound verb 「さし引遺り」 can be broken down as 「差し引く」(“to deduct”) + 「残る」.

「立かへり」 of course comes from the verb 「立ち返る」 ("to come back").