Where I live is notorious for steep inclines and my normal riding takes place on this terrain. We have some of the famous testing hills that were sought out in the 1920s (Porlock, Lynton, Beggars, Countisbury etc) so a 1 in 4 with a sharp bend at the bottom is fairly normal here. Because I don't have the EW on the road yet I can only offer some generic observations for machines from the 1920s.
Going up is usually not a problem with late vintage machines with gears and a healthy engine and taking it easy in first is better than labouring in second. You shouldn't need the clutch. Some like to give a squirt of oil before starting the ascent although depending up on the engine design some machines seem to splash more oil when the engine is tilted back (the 350 Enfield for example) so maybe someone can tell us how this affects the EW? You should carry spare plugs just in case you do 'over oil'.
Going down is the one that matters and only you can tell us how good your brakes are and how badly they fade. I try to always descend without using the brakes too much and keep the brakes for stopping at the end or for an emergency which leaves the engine to do the work and depending upon the [incline, weather, traffic, compression, gearing] I'll select either first or second.
Using the engine as a brake can cause a lot of vibration. The Brown & Barlow float need often dances a jig when the revs are high in engine braking mode which creates a flood and sometimes jams the needle 'open' so I'll usually turn the fuel tap off before descending. It is also worth checking everything at the bottom to see if anything has shaken loose. Check carbide mixers, exhaust nuts, petrol/oil caps and all of those small things that can unscrew themselves.
