Assuming this just puts "me" back in time, where I can interact with the past, and perhaps alter things (whereas interacting with your past "self" would be a sure-fire to either kill or drastically alter your current "self"), I think other than joyous spectator-ship, which I would probably need to research to find anything sufficiently interesting, I would make the obvious choice (in a few easy steps):
1. Look up some stock market history
2. Find someone that I trust, or depending on how short-term I can make this work effectively (if this thing is multi-use, start with a small test), use myself
3. Go to the past
4. Get that person, or myself, to invest some money into the stock market in such a way that it wouldn't have much of an effect on the market itself over the span of time we did this for
5. Return to the future, collect profit
6. Monitor/consider any noticeable ramifications before further attempts (this includes things like making sure people don't catch on that my activity is suspicious)
There are many ways you could go about this, most people would probably first think "lottery!" but that draws a lot more attention, and you can't really do a small test first. Like this you could easily pull in a few dozen grand here and there without anything looking too out of place. ;)
TL;DR: I would use a time machine to cheat at life. I swear though, some of the things I would do, if I thought I could get enough income this way, would be at least somewhat noble... OTL