Many poker books such as the Harrington on Holdem series include images of tables showing the current situation as a visual aid to the questions asked. It would be great if there was something like that which could be generated by a plugin on the ask question gui.
I like that these make it really simple to create a hand history, just a copy and paste. If it takes a half an hour to ask a question that uses this tool, it's not that great of a tool. Without question, a copy/paste and/or graphical creator is necessary, to mark up an entire hand on your own will just take too long.
I do not like that these plugins focus on eye candy. When I see a flashy and fancy table image with animated dealing cards etc, I have to adjust to reading that table, which is almost certainly different than my normal visual representation of a table. Also, with the animated table style, I find it difficult to follow the question being asked because I instead just follow the hand animation and build my own thoughts. A more bland, black and white circles and boxes table design with emphasis on the pertinent information is much easier to digest across the various game styles.
Poker isn't just hold'em, we need to support as many of the casino available games as possible. A great way to do this is to remove the cards from the view as much as possible and have people add them as part of their write up if they are important. I'd strip it down to the basics, and just use player names, possibly pre-generated, button position if appropriate, stack sizes and the actions in the current round up to the current point.
I've been looking for something that works like this, however I haven't been able to find it. I'm also not particularly excited about any of the hand replay tools I've seen out there. I'd love for replies in this thread to list what information they think is useful in a hand history or situational widget, to see if we can really narrow down what's important.