This One

A drill pump will work, they are slow and they don't prime very well but will eventually with hose manipulation. They wear out pretty fast but at $4 a pop doesn't really matter.

I think your wondering how to get the VO you currently have in there, out. If you only have bung holes (careful) to work with and you can't lift it, a drill pump is probably your best bet.

After you get the VO out....

You need some sort of bulk head fitting for the base of your barrel.

Or better yet, if your barrels are like mine, the bung hole caps have threads built in. Look very closely at the cap. If you cut out the center 3/4" out of the center your left with a 3/4" threaded hole (if your careful enough not to cut into the threads during this process).

Now, flip the barrel upside down and you can put a 3/4" pipe (black works best) in the threaded bung hole. Cut a hole in what was the bottom and is now the top.

If this sounds like something you wanna try let me know, I have more tips for you. If ya want I could post a picture too.

Mccrea,
I got a stock oil pump from Autozone for a Chevy small block (1969 Nova with 350 engine) for about $15. They are nice gear pumps. Drilled out the intake & JB welded a several inch long piece of 3/8" dia black pipe into the hole. (Drilling was easy as the pump body is soft cast iron). Next drilled a new hole for an outlet & did the same thing. Plugged the original outlet with JB weld & also the bypass passage. Reassembled the four pieces of the pump with bearing grease on the shafts & gears. Shot some paint just to pretty it up. 5/8" garden hose slides right over the black pipe & gets a hose clamp to keep it in place. The pump shaft is 1/2" so it will chuck right up in a 1/2" electric drill (you can use a battery powered drill for collecting oil). I just emptied a collection barrel with 35-40 gallons of partially hydrogenated oil in about 10 minutes with a drill running at about 550 rpm. Higher rpm = faster pumping or hook it up to an electric motor at 1720 rpm. The pump is supposed to be self priming but it didn't pull the oil probably because the hose was into the heavy bottom layer of hydrogenated oil & it was about 55*F. I just used a funnel to pour some oil into the short pickup end of the hose to fill the hose & prime the pump, dropped the hose back in the barrel & pulled the trigger on the drill. Pumped the collection barrel dry no hassle. I've got two of these & they work great.
Blaise

Maybe you could get one of those priming bulbs that you squeeze, they look like a grenade? (Outboard engines usually have one)