言いたいところだ: Similar to English "I would say"?

Question

This comes from the anime Black Lagoon where A and B are smugglers who are upset that a newer crew member isn't willing to do more dirty work (he cares too much about morals etc.) for the business. He was chosen for a specific job based on his previous company experience:

A:やっこさんもちっとはさまになってきたかい ？ と言いたいところだが何のことはねえ
奴のホワイトカラー ･ ルックに ― 全くお似合いの仕事だったってだけだな
B:今のところはな
A:So the troublemaker is being useful.
Well, I'd like to say that, but nothing's changed. It's just that his white collar look was perfect for this job.
B:Yeah, so far. [show's translation]

Can this usage of ~たいところだ be used similar to the English "I would" construction
as in "I would say...." or "I'd like to say that... but"?

I found this explanation that tries to explain the difference between 「したいです」and 「したいところです」:

「したいです」は積極的な気持ちです。
「したいところです」は、したいという気持ちになっている、という意味で気持ちは変わるかも知れず積極的ではありません。
「買い物をしたいところだが今日は込んでるので止めよう」など、結局はしない時に使います。

I also found this explanation:

｢今日は思い切り遊ぶぞと言いたいところだが、明日からテストだから勉強する｣
→自分の気持ちとしては｢思い切り遊びたい｣が、我慢して勉強する。

This part about it being used both when your feelings of wanting are subject to change and that you often use it when you ultimately won't or cannot do the action seems very similar to my understanding of English "I would [verb]".
Explanation 2 having 自分の気持ちとしては also points to this.

Question 1: What does たいところだ really mean in these contexts and what is ところ contributing?

Question 2: Does たいところだ really work like English "I would [verb]" or "I'd like to [verb]"?
For example I wonder how it differs from these two usages of "I would" marked under "Possibility".

Answer 1

tl;dr: I would say so ;)

The translation is reasonable. I think that, once the underlying meaning is understood, this is really more of a question about English than about Japanese.

~たいところだ straightforwardly breaks down as the ordinary suffix ~たい plus the common word ところ plus copula だ. ところ does have some idiomatic use, but the most literal meaning is "place" - then it's used to refer to various kinds of places, ranging from the literal (like a street address) to the abstract.

Here, we can think of it as meaning "situation" or "circumstances", thus: "this is a situation where I want to say...". But ところ following a non-past verb is also (as you found) simply understood as an idiom for "about to ...". (Hopefully, it's clear now where that idiom comes from.)

This emphasizes the underlying conditions: the troublemaker has a white-collar look, which was convenient for A, and thus A has some desire to offer praise - but has not yet acted upon it. (Of course, A does quite literally say やっこさんもちっとはさまになってきたかい ？, but this is just rhetoric.)

In context, this is followed by a conjunctive が. Thus, your proposed "I'd like to say that... but" is in fact quite literal.

English speakers typically just think of "would like to" as a phrasal verb that's essentially equivalent to "want to". That's more or less what's going on here. There's a conditional or hypothetical sense introduced by the fact that nothing has actually changed, and thus it wouldn't be accurate to say that the troublemaker has become useful. In English we also shift to this phrasing because there's some other cause to hesitate in expressing the desire to do something - for example, because of socially-imposed restrictions (i.e. it would sound too selfish or presumptive to state it outright).