1: what is the normal operating temperature of a 289
2: at what temperature should i get worried
3: Does anybody run an electric water pump with powersteering and how does the belts line up?
4: are holes required in a shroud with an electric fan to help cool at highway speeds since the fan being ON, could be a restriction.

My setup:
- 3 core (i think?) aluminum radiator with a 14 inch fan setup.

- factory everything else.

 

1) 200-215F
2) 220F+
3) I wouldn't recommend an electric pump for street use. There's not much point, and it's just one more electrical part to worry about failing. A good high-flow mechanical pump will do you just fine. In fact, a good standard pump will probably work just fine.
4) You should have your fan wired up to a thermostatic fan switch operating a relay, so that the fan only comes on if the coolant rises above a certain temp.

Also, I don't really like that 'shroud'. It looks like more of a restriction than a shroud. A shroud will space the fan away from the radiator a bit to allow air to flow through the radiator. That shroud looks like a piece of steel plate with a fan bolted to it, essentially making the area of the radiator covered by the shroud useless.

 

i think my fan comes on at 160ish, but it will not turn off untill the car turns off, simply cause it wont get back down to 160 while driving.
do you think cutting "speed holes" will better suit the shroud? i agree with it being a restriction

 

The fan shouldn't come on at 160F. 210F would be better. The idea is that it shouldn't be running until the temp rises.

I don't know about drilling holes in it. Not sure what that'd do for airflow. If it were me, I'd be looking for a better shroud/fan. That thing doesn't look like it flows enough anyway. You need a fan that flows at least 2500CFM. Mark VII and Taurus fans are common swaps because they flow so well.