Jamie, first off, welcome to CHR. 2nd, there are no dumb questions.

Straight axles will never be a top notch ride and good handling setup no matter what you do to them. Others here may argue the point, but how many modern cars are built with straight axles vs. A-Arm suspension??? An IFS set up for the front could in the long run be the best way to go. You will get good handling, good steering, and good brakes. I put an IFS under a guys '54 chebby panel last year, he had to machine a pulley on the water pump pulley to get the power steering pump to work on the car.

I'm not a chebbie guy, but if I remember correctly, the dipstick is on the left side of the motor, not sure but some chebbie guy will be along to correct me shortly, I'm sure.