Could be a bad O/D switch on the shifter. You'll want to pull the console panel where the shifter is and replace the shifter bushings (Toyota, cheap part to fix it), makes a world of difference if the shifter is showing side-to-side sloppiness. While you're in there take a look at the O/D wiring and maybe clean up the switch if you can get to it.
This is definately not a tranny problem, though like you said it wouldn't be a bad idea to have the fluid changed. BTW, you don't have a filter, just a pickup screen iirc.
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