Does the inlet line from the top of the oil filter fasten to the tee fitting that has the oil pressure gauge line?
Yes, the correct direction of flow puts the oil from the same port that supplies the pressure gauge to the middle of the side of the filter canister, and the return to the crankcase comes out of the bottom fitting. The 1/16" diameter hole in the standpipe controls the flow, so theoretically, the lines could be connected either way and the filter would still work.
Jerry