Jim, since you're mostly working in a Maker space environment, I assume you're carrying in your tools. A 115 piece set is nice but the case is big and heavy. As an option, I suggest you buy the bits in smaller sets. I would buy a 1-60 wire size set first; most smaller holes for tapping screws use these drills. I would buy a fractional set second and a letter size set last. You will need all of them. Buy them in full sets.
Jobber drills are longer and are fine for most work. If I could only have one set, however, it would be a screw machine set. They are shorter, stiff and accordingly more accurate (shorter lever arm). Their length is enough for the vast majority of holes you will drill.
118 vs 135 - both work. Most drills for general work are 118 degree. I have both and both are fine but I find the 118 to drill with less pressure.
HSS vs cobalt - HSS is fine for 99% of your work. Cobalt is really good for stainless or more abrasive stuff but they cost more. I have a cobalt set that I use only when I plan to tap a hole in stainless steel; I push these drills harder so that they cut continuously in the hopes of reducing work hardening. If I'm not going to tap the hole, I use HSS in stainless.
Buy a good 1/4" spotting drill; 120 degree if you use 118 degree drills and 140 degree if you prefer 135 degree drills. They will improve your accuracy re hole location and save your edges.
A Drill Doctor is a good idea if you haven't had a lot of experience grinding drills on a bench grinder. I picked one up because I don't see as well as I used to and grinding smaller drills was becoming a chore. This is a cheap machine that does a decent job and its fast. If you use your drills properly, it won't see that much use so I think its a good investment.
Keep in mind that when drilling, speed is not as important as feed. You should be pushing the drill hard enough so that it is cutting continuously. Most of the wear on a drill comes from spinning it in the hole without cutting. On large drills, I am running slow and pushing it hard. When I'm done, I can only feel a little heat in the bit when I take it out of the chuck. If you cannot keep up with the feed, slow down the speed.
For brands, there are some good ones: PTD, Titex, Cleveland, Triumph and others. I have all of these and more. Makita had a really good fractional set that they no longer sell; it is still may favorite set. Do your homework on brands - the guys will be able to advise you.