Really dirty gas from my fuel line?
 

I unhooked my fuel lines from the tank to check the fuel sender and the fuel that drained back was black!
What gives? Is this typical since it's coming from filter (I presume?)

That's why you have a fuel filter. If you work on enough cars, you will see everything in the gasoline sooner or later. The filter is doing its job, and it sounds like it is doing it very well. If you don't have a lot of gas in the tank, you might want to drain is completely to flush out all the crap and install a new filter too, which you will most likely do anyhow.

So I'm oaky for now, but should change it soon? Fall/winter project...?

It is totally up to you. You have it apart now and can change the filter and clean out the tank and be done with it. Or, if you want to do it later, it is your choice.
The early 986 like mine, have the filter in the center of the car, relatively easy to get to. I think the newer ones have the filter in the tank if I remember correctly. Someone else want to chime in if this is correct.

spinnaker is saying right that its totally upto you.

As long as you're in there, you might as well change out the filter and know exactly when it was replaced last.