If you have some time it would really help to read the Berkshire Hathaway Annual Reports. These would give you everything you need to know about owning individual stocks. To sum it up:
- buy companies you understand and that have a huge competitive advantage
- think of yourself as an owner of the company, not just a speculator of the stock
- if you see a discount buy big
The rest is commentary.
Now, for your specific question, there is a lot to consider about your decision if you want to make it complex. Then, there's a simple way to consider it:
Does the company have a competitive advantage so that they will be around and putting out dividends long enough to make this work?
Is the company selling at a discount to what it's worth?
What trade-offs in potential returns from other investments am I making my putting my money here?
As for Vanguard, you may want to use them as a brokerage, but there are far less expensive ways to invest. I use MB Trading ($2 per trade), there are free trading apps you can use. If you have no intent of ever trading again, then stick with Vanguard. If this is something that you're interested in doing in the future, then consider some low-fee trading services.
Best of luck!
Long 14 company individual stocks, as well as a huge advocate of Vanguard Funds. One is for fun, the other for FI.
J-