@krickard,
Hey, I am brand new here, but have been listing on Ebay since 99. The way i do it is i separate items that you know have a better chance to sell at a good price when sold started at .99, and ones that you are not so sure of. For firsts, look up those same items you have before you list them and take notes(in your head or on paper is acceptable). Make sure you see what the "completed listings" are for it and take note of how much shipping was charged. If you know it will get bids, then take that .99 cent chance. Also, when people bid on stuff, it is like a competition to many of them and they do not like to lose. So more hands on it, means more people will not like to lose. Many listings you need to take a chance with and some-no. the ones you do not want to take a chance with, then you need to figure out the absolute lowest price you would take for it, and even go slightly lower than that and cross your fingers. People do not like reserves because it guarantees them nothing, and many sellers use that with no intention of selling the item, but just seeing how much they can get for it-hence Ebay lets people know that many buyers do not like it, as it costs Ebay money by items listed, but not selling. Take your time with stuff and do your research, no matter how long it takes you, and it will pay off. I have been doing this for years, and just joined this community an hour ago, because you can never have too many resources. If you are not sure of some of the stuff you have--It seems like you are in the right place for help.
Finally, in your post you said you have a bunch of stuff from your parents house, which means you did not just blow a wad of cash at an estate sale or such for it, so after you do research on your items, consider it found money and take a chance on some of it, and if you know you have high ticket items, use your due diligence and make some cash.
I hope this helps, and if you have any questions i am here to help too!