No insurance runs are risky for sure, had to do a bunch of those, especially when you come across a rare upgrade...
I'm using a trade site, but I'm not only using it, I'm also updating its database on a regular basis. It took me a week to map out my homebase and its adjacent systems, and by the time I finished feeding all data in the database the trade data of the first stations was 6 days old and therefore as good as unusable...
I used the trade site to my advantage 887 times, but to keep it up to date I updated the database 3766 times. Updating can take from 20 seconds (just updating a price) to half an hour (adding one station, all its services, commodities and prices). Its quite time consuming XD