yes drain the oil first then take off the filter. (drains better when oil is on the warm side) it will still be a mess because some oil is still on top of the filter housing but there is that little runway for the spilled oil to drain down. (which isnt long enough IMO). and yes put some oil in the filter before reinstalling it. and as you can notice from the pic above the filter is at an angle so you cant fill the filter up all the way. bout 3/4 full. and take your finger and dip it in some of your new oil and lube the o-ring thats on top of the filter to get a good seal on the mating surface between the filter and the filter housing. the filter does not need to be wrenched on there really tight either. just get it a little more than snug. you'll be fine bud. just take your time, dont rush it, and dont forget to put the drain plug back in.