chat

I have examined

"I have thought" was the intended reading, but good job at understanding that it was the perfect aspect.

on top outside

上外 is how I chose to render the word "about", which etymologically means "on-by-out" — so I represented the "on" part with 上 and "out" with 外 and dropped any representation for the "by". You can also think of 上外 as a sort of rebus: "up-out" sounds almost exactly like "about".

this askation

"this question" was the intended reading, but good job picking up on how I was using the nominalizer 子 to represent the suffix -(at)ion. In hindsight I guess I probably could've used a better character than 問 for the "quest" part, even though "ask" was what quaerō meant in Latin (also related to our "query"!) and the Old English word that question displaced was āscung (lit. "asking")

a number of times before

"sometimes before" was the intended reading, but I honestly really struggled with finding a good enough way to represent "some" and figured that if it could also be read as "a number of times" that the meaning was close enough to the intended one anyways. On the other hand I didn't mark 時 as plural in any way.

I commonly closeation

"my conclusion" was the intended reading. So I opted to use 共 to represent the prefix con-, and then the "clus" in "conclusion" actually means "close", and is in fact related to our word close via Latin claudō — so I used 閉 to represent that part. And you already gathered that 子 is equivalent to -(at)ion.

I had considered that not explicitly marking 我 as possessive might be confusing, but if you have words in Chinese like 我国 for "my country" that it was probably good enough.

is that you could do them

"is that you could do it" was the intended reading.

in outside not very good.

"but not very well" was the intended reading. Interpreting "well" as "good" is reasonable enough, since a lot of people treat these words as interchangeable, anyways.

The word "but" etymologically means "by-out", hence 在外. You correctly ascertained earlier that 在前 meant "before", and the 在 in that represents the be-, which also etymologically means "by". Admittedly 在 which means something closer to "in" or "at" wasn't the best choice for "by", though.

"But" was another word that was very tricky to find a way to represent. I'd also considered doing some sort of rebus with characters for "butt(ocks)" or "(head)butt" or "butt (of wine)", such that I could ideally avoid splitting one word across two characters, however that sort of rebus would just be confusing if not vulgar... Not that 在外 is that much less confusing, though, but at least it conveys well enough that it's a function word.

So all in all the original sentence was

"I have thought about this question sometimes before, and my conclusion is that you could do it, but not very well."

...And your interpretation basically proves the point. Although to be fair if English were written with Chinese characters, there would probably be a lot of 国字 which would make the system a lot smoother, and oftentimes if there's a bit of ambiguity in the reading it isn't that big a deal.