Two points to share:
1) Get legal advice to understand the nuances of the different licenses perfectly. I can't emphasize this enough.
2) Chances are that when your licenses will really get examined is before an acquisition or funding event. Depending on the sophistication of buyer/ funder this could range from light diligence to an "enhanced pedigree."
"Enhanced pedigree" implies that not only the license of your open source software, but the licenses of the software that it is based on or modules included within it..and the licenses of the software that is based on, etc.. Sometimes digging several layers deep uncovers an unfavorable license which will require remediation before moving forward.
These can often go un-declared in software and only turn up when scanned by a tool like BlackDuck. I have had people try to talk down the price of acquisition based on some sticky licenses buried deep in my software...
It's great that you are asking the questions now, and I definitely think taking time to do it right up front will pay off in the long run.