I like the idea of automatic buy and sell. Just, isn't sometimes crypto so volatile that you get your stop buy/sell orders triggered by a short spike, if you see what I mean?
Also, I heard you have engineering experience... ever considered trying a trading bot? You can run simulations on past data and create a model to apply to the future, tune existing strategies, no coding experience needed, else you can also code your own strategy of course.
Recently I got involved in this project and I can recommend you to give it a try, there is also a "paper" mode (real time trading, but no trade done, only simulated) which I recommend to see how good or bad the bot is. I think you may understand it quite well and tune it better than me.
https://github.com/DeviaVir/zenbot
It works better on linux/mac, but you an get it working also in windows of course. Maybe I'll write soon a tutorial on steem just to get people started and give it a try on "paper".
There are many other bots, but I liked this one because it's open source and I tried another one without success, so I stick to this one for a while at least to learn how it works. It can also send you signals if you don't trust it to trade automatically for you.
Let me know what you think.