That "around the houses" routing of oil pipes looks like someone shouting "Hey, look at my ultra cool bolt-on oil cooler!". Purely fashion in my personal opinion, a bit like pointing at your left ear with your right hand. I'd be looking for the shortest, most protected route from the block to the cooler, and then tie the lines down properly to stop them fretting.
On the "it takes longer to get oil to the bearings on startup" - this will only happen if the oil coler drains back to the sump when the bike is not running. There's not much of a head difference between the cooler and the sump, and no obvious route for air to get into the cooler, so it will *probbaly* remain oil filled - which means near instant delivery of oil to bearings on startup. May be different after a long stand, or if the system has been opened up, in which case it'll need to refill before delivering a steady oil supply to the bearings.
Oil pumps are gear types, so principally positive displacement pumps. If in good condition, for any given rotation speed, they will pump the same volume, only pressure (eg. due to longer hoses) will increase. This becomes less the case as the pump wears, when it starts to behave more like a centrifugal - more slippage at higher back pressures. The length of the lines will probably hardly be noticed by the oil pump - but I'd still keep them short...
Ian