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The `〜そう` form means "seemingly 〜" and is usually conjecture made based on
first-hand information. This usually means seeing something or hearing about
something and making a conjecture, e.g., `おいしそう` when seeing the food.
(Presumably, first-hand information would extend to ESP, psychic visions,
etc., if you believe in that.)

Now, it's hard to imagine that this would ever apply to `かわいい` based on visual
first-hand information; since you're actually seeing the thing, there's no
guessing about whether or not it's cute. However, it would be possible to make
a "seemingly cute" conjecture if the first-hand information was hearing a
description of something. For example, maybe your friend is describing their
new puppy to you. Upon hearing the description you might respond that it seems
cute.

By the rules, `かわいい` (sometimes written `可愛い`) would then become
`かわいそう【可愛そう】`. Unfortunately, this coincides with `かわいそう【可哀想】` meaning
"pathetic; pitiful; sad".

  1. Is the "seemingly cute" `かわいそう` even used practically in the way I mentioned (or some other way)?
  2. If so, is context enough to distinguish which of the two words it's actually supposed to be? Or should you just avoid it altogether? Because I can think of a context where it would still be ambiguous.

> "My new puppy is small, and fluffy, and likes to play ball. But a cat
> attacked him the other day".  
> "かわいそう" → (Is it "Seems cute" or "Poor thing"???)
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word-choice nuances homonyms ambiguity
"Seemingly cute" - かわいい + 〜そう
From what I've read, the original meaning of "かわいい" had less to do with
"cuteness", and more to do with inherent qualities such as weakness, small
size, docility, etc., that engender a feeling of pity. As far as I recall, the
change in meaning to "cute appearance" is fairly recent. So it could be that
either "かわいそう" just hasn't caught up with the new meaning yet, or is useful
enough retaining the older meaning that it's unlikely to change.

Additionally, as a conjecture (and keep in mind that it's just a conjecture: I
don't feel 100% confident about this), I think there may be a tendency to use
~そう to express qualities that are not immediately visible, i.e. that are
inferred rather than seen. For things judged by outside appearance only, it
may be that the construction "~く/に みえる" is more natural. So, in your example,
maybe "かわいく見える" would give the "It looks cute" meaning. My sense is that
"かわいそう" doesn't give this meaning.
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First of all, I do not think that people use かわいそう to mean “seemingly cute.”
But I cannot pin down the reason of this.

I think that it is at least partly because かわい+そう would have the same form as
かわいそう meaning “pitiful.” However, I am not sure if this is the only reason.

As you noticed, かわいい describes appearance. I cannot think of a context where
白そう or 青そう (or other colors plus そう) is used naturally, and it does not seem
to have anything to do with ambiguity. This may support an argument that
かわい+そう is not used because かわいい describes appearance.

However, 明るそう (“seemingly bright”) is used (and it is not limited to
figurative usage such as 明るそうな未来). For example,

> [いかにも明るそうな電球でした。](http://www.waride.net/hakodate.html)

(This example describes large lamps on a squid-fishing boat, which are used to
attract squids at night. Because the author saw the boat during the day, the
lamps were not turned on and the author described the lamps as “seemingly
bright.”)

>
> […ルームランプを消費電力が少なくて白くて明るそうなLEDに変えてみました。](http://homepage2.nifty.com/mmas/legacy/diy-
> lamp.html)

(Here an LED room light is described as “seemingly bright” probably because
the description is from the perspective at the moment before the author
changed the room light to the LED light.)

This means that そうだ meaning “seemingly” can be sometimes attached to a word
describing appearance. This is why I am not sure about the exact reason why
かわい+そう is not used.
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My answer builds off of rdb's answer.

My understanding is that ～そう for usage of "seems" cannot be used for actual
information that is apparent. I.e. you can't say "she looks cute" using そう for
someone you are looking at. Though, you get on the slippery slope when you
want to say something like "she sounds cute" after you get off a phone
conversation. But then I think you'd use the "～く/に 聞こえる" grammatical pattern
for that.

In terms of using "～く/に みえる", rdb is right in that gives a completely
different meaning to what you are looking at. I have always thought about みえる
as saying "She looks cute (but normally doesn't/shouldn't)" connotation built
in.
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I hear かわよさそう used frequently as a substitute for かわいそう, and sometimes its
altered companion, かわよい. I presume it's _very_ slangy and I feel perhaps a bit
feminine, but it does exist nonetheless. Another workaround might be to use
可愛{かわい}らしい, which while technically different, at least approaches the
intended meaning. As for _when_ it's used, I don't think it breaks any
conventions. I usually hear it when something sounds like it would be cute.
Clearly this change is taking place because of かわいそう having the alternate
meaning, but I think this is evidence that the concept of modifying かわいい in
that way at least isn't abandoned entirely.
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