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These two phrases seem to have very similar usage and I'm unable to determine
the difference between them.

The examples I have are:

> 彼は服装 **からして** だらしない。きっと他の面も同じだろう。  
>  _kare ha fukusou karashite darashinai. kitto hoka no men mo onaji darou._
>
> 症状 **からすると** 、心臓の病気かもしれません。  
>  _shoujyou kara suru to, shinzou no byouki kamo shiremasen._

However, both of these phrases seem to translate to the English word "from" or
"based on". I've asked a few Japanese friends about the difference, but they
were unable to explain it eloquently.

Is it possible to switch からすると and からして in the preceding examples? Will it
still be grammatically correct.

(Additionally, からして seems to have the meaning of "for a start" as in
ひらがなからして読めない or "For a start, I can't even read hiragana." But this usage
seems to be completely separate to the "from" or "based on" usage.)
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word-choice grammar
Is there a difference between からすると and からして？
I learned them as an interchangable set (along with からすれば thrown into the mix,
though that one sounds a little bit more formal to my ears), and the two
grammar reference books I just checked don't list any nuance differences
between the two. One difference is that adding a も for good measure after からして
works better than after からすると, though I don't think it's entirely
ungrammatical. A more formal explanation for this sense of the construction is
that Xからすると/からしてY means X (a noun phrase) is something perceivable by the
speaker, and Y is a judgment based on that.

It should also be noted that the construction carries one more sense for both
forms (separate from the alternate からして sense you mention): "from the point of
view of..." as in

> 一般人からすると、この値段は高く感じられることかと思います。

(usage example provided by Google).
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As _@Oren Ronen_ mentioned, there are actually two different grammar
constructs concerning this.

Case 1: **～からして** , meaning "beginning with". This is used in a list of
examples (often incomplete), primarily in a negative context.

>   * 私はあの人があまり好きではない。下品な話し方 **からして** 気に入らない。 -- I don't like that guy very
> much. Starting with his vulgar talk, he just doesn't sit well with me.
> (indicates possible other negative aspects about the guy, even though they
> aren't listed.
>

Case 2: **～からして（も）** ／ **～からすると** ／ **～からすれば**. These mean, "thinking about it
from the standpoint/position of ..."

>   * 米を作る農家 **からすると** 、涼しい夏はあまりありがたくないことだ -- From the viewpoint of farmers
> that produce rice, cool summers are not a very good thing.  
>
>   * 芸人とかタレントなど **からして** いつもファンのためサインするのが大変かもしれない -- Thinking about it from
> their view, it must be tiring for entertainers and celebrities to always be
> signing autographs for fans.
>

Now, in case 2, the three forms are definitely interchangeable (with the
nuance of adding **も** to form ～からしても -- "Even from the standpoint of..."),
and in fact, they are grouped together for this definition. However, for case
1, I don't believe they are. I've only heard of case 1 using **～からして** , but
maybe I've just never encountered this meaning with the other forms (any
natives feel free to correct this).

Your first example seems to be case 1: the first negative point about the
guy's "slackerness" is his clothing. So here I would say they are not
interchangeable. But your second example seems to be case 2 ("Looking at the
symptoms, it might be a coronary illness"), so you could use **～からすると** or
**～からすれば** here.
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