Don't worry too much about long radiator hose lengths. There are thousands of VW vanagons out there that are longer than most soobs and have a radiator in front and an engine in back. Also, just because the loop is long, doesn't imply you need a booster pump. The regular water pump is more than adequate. If you need a good hose to run long distances, try marine exhaust hose. It is super heavy duty. It is reinforced with a metal coil and has a tough fabric cover. It's a little expensive, but not too bad when you consider the convienience. A boat supply shop can help you, or you can buy it online. If you buy online do a lot of searching. Prices are all over the map.
Oh, yeah about bleeding. Its not rocket science. Just be sure you tee-off isolated high spots with small bleed hoses to collect air and send it back to the your radiator or resevoir where the radiator cap is.