The benefits to running a remote oil filter system is you can place the oil filter in an easy to access area and it is a spin on type oil filter.
You should be able to access your current oil filter with the engine in the car.Time to jack the car up, again (LOL!) and crawl underneath.
As far as priming is concerned; If you are draining just the engine, replace the filter, fill the oil (about 1/2 way up the oil inspection window) and turn the engine over with the ignition switch off (so it won't actually start). Although, I have just started the engine and let it run at an idle.
If you are draining the whole system (oil cooler and lines), then you will want to fill the oil cooler and dump in what you can into the oil lines. Again; Spin the engine over with the ignition off.
Steve