1. The best pumps with a depression for a nipple at one or both ends are (by reputation -- I've never used either though I've owned both) the HPX that you already know about and the Silca.
2. I carry a pump for the use of riding companions (holding thumbs!). It's the only miniature pump I have experience of that works, the Topeak Peak DX, though it could be bigger for my 60mm tubes, but you get there in the end. Beautifully made, suits both Presta and Schrader valves without changing fiddly components, includes excellent bracket to fit under water bottle, made of aluminium but light enough for a touring pump.