I've been in this hobby for a very long time and have drilled, reamed and bored in most materials a hobby guy is likely to encounter. In all this time, HSS drills in 118 degree points have served me well. I have, but rarely use, my cobalt drills and since I tend to center punch or spot drill my holes, I don't have a strong need for 135 degree drills (although I own them). I drill stainless often and a sharp HSS drill handles it fine; it is more about speeds/feeds, lubricant and technique than the drill material.
Do not think that a cobalt drill will drill all holes successfully without a brain in YOUR head. Cobalt merely handles higher temps better than M2, that's all. You still have to use the right speeds and feeds. Also, there are times when screw machine drills are the ticket and times when jobber drills are needed; I have both and need and use both. If I had to pick only one length, I would get jobber drills because there are times when you need to go deep and screw machine drills just won't get it. Screw machine drills are more rigid, true, but they are not a panacea.
My advice is to buy drills in fractional, wire, letter and metric, in that order. I would buy them from reputable makers only and I would buy them in the point geometry you prefer; both 118 and 135 works. I would also buy some cobalt spot drills to suit the geometry of your drills. You can opt for cobalt if you choose but for probably 90% of the work you are likely to do, HSS will be fine.
Learn to sharpen your drills. Doesn't matter what you use to sharpen them as long as they are sharp.
Don't spend big money on reamers unless you are doing work that requires them frequently. They are expensive and for occasional use, buy the ones you need or learn to bore accurately. The wabbit hole is deep indeed, but this is one place where you can avoid some cost.