If you have a decent scale, you can send everything priority mail... the post office will deliver everything - boxes, tape, labels right to your door, for free. If you sell a lot on ebay, you can do 100% of the shipping from your home - the post office will pick up the package. To calculate shipping via priority, all you need is the customer's zip. (And, it's a piece of cake to include a shipping calculator on your auction so the customer only has to enter their zip code.
If I'm not mistaken, I think the packages are automatically insured for up to $100. (I may be wrong.) If the item is worth more than $100, there's no way in heck I'm going to ship it without insurance, and I feel that's the customer's responsibility. If it's a relatively expensive item, I get return receipt - something I feel is *my* cost of doing business. All you have to provide is wadded up newspaper or bubble wrap, or whatever for padding - depending on the item.
Personally, if I'm given the choice of bidding on 2 auctions, I'd rather pay an extra $1 overall to someone who charges the actual shipping fees than to bid less, (and make up for it in slighly excessive shipping costs) - even if I'd save a dollar. I'm sure there are many who feel the same way I do. It pisses me off to see someone with $25 shipping on a $10 item. (whereas other sellers have it for $30 with $5 shipping) Yeah, I know how to factor in shipping, I just think those types of people (excessive shipping with the idea of just calculate in the shipping costs are a. lazy or b. trying to cheat the system. I really wouldn't want to be considered a member of either group.