Here are my thoughts and opinions on the Shakey Head.
While I think that this technique being a finesse technique originated in a clear water environment, I have used it with success in stained water. I have not had to much success in muddy water with it (mainly because it is more of a sight based technique for me). It can be used in any type of water as far as I am concerned, and on any type of cover. I have used this in water depths of 10' and less because that is what I have around me (this is why in some of my fishing reports I list a 1/16 oz Shakey Head), it DOES work deeper you would just have to increase the size of the jig head. I am not sure about cypress trees, I have never personally fished them, I am sure that someone with more experience will chime in with some more info.
Here is what I use, take it as a sales pitch I really don't care, it's not meant to be. 1/16oz Shakey Head, Shakey Worm (because they FLOAT) (Both from Hookerz Tackle, a BBC Sponsor) Light line is a must I use 10# Fluorocarbon this year, I just started using the new Vicious Line, I am still up in the air on it.
6'-9" Mag Light casting rod (light tip, plenty of backbone to drive the hook in) Shimano Scorpion 1000. I have caught fish (among other things) in August with 90 degree water temps and in December with 30. It works all year, you just have to vary your presentation to how the fish want that day just like anything else.
I primarily use only use two retrieves:
1 (inactive/neutral fish): Cast out and let it sink to the bottom, and rest for about 30 seconds. Shake your rod tip for about 5-10 seconds and stop, let it rest for 15-20 seconds and repeat all the way back to the boat, shore, or until you are out of what you think is the strike zone.
2. (Active Fish): Cast out and let it sink to bottom, I will continuously shake my rod tip, but not moving the lure horizontally very much, giving the appearance of something feeding on the bottom ( I use a little bit heavier jig head for this to maintain bottom contact)
Now for fishing laydown, and bush piles, I will Texas Rig the shakey worm on a smaller EWG or J Bend Hook to achieve the desired tail up appearance. Now you have a lure that is more weedless than a jig head that can be fished through trees and such. On my Texas Rig I will put a Glass Bead like what you would use on a Carolina rig in between the weight and the hook and peg the bead, when you retrieve this the weight banging against the bead will click, which works even better if you use a craw imitation instead of a worm.
Below is a picture of the way that I rig a shakey head on a jig head, this is from the Hookerz Tackle website.
Sorry to be so long winded