My mantra is: "When you book on your own, then you're on your own" which applies to making dining reservations, dealing with problems, etc. Online agencies will place your order, and then, they're done with you. Support is not their strong suit. Some travel agencies are like this and are not as concerned with customer service as they are with making new bookings; you have to have a relationship with your TA to know the difference.
Another good phrase is "if something seems too good to be true, it probably is" but many online companies 'hook' people with offering discounted rates that usually end up not being such a discount when everything else gets added in. I often see ads that say, "Visit XXX for only $XX per day!" which is really enticing, but it is nothing more than a hook because it's the per-day rate before mandatory fees and taxes are added in. People get excited about that type of marketing and after investing a bit of time in the booking process, they tend to complete it because they're already down that path; that's what those online companies are counting on, even when the end price is much different than what the consumer originally thought they'd be paying. Every once in awhile, I do the math, and I figure out that the 'hook' pricing is equal to what's available elsewhere, or even more expensive, but I'll tell you, people really focus on that 'per day' aspect and think they are really getting a deal. Isn't it better to tell people the total that they are going to pay, what amount is going to show up on their credit card bill up front?
I always encourage travel insurance, no matter what, because life is unexpected. Having insurance has saved me thousands of dollars due to unexpected circumstances.
As far as name changes go, particularly with airlines, you really have to be specific when you are making your reservation to have the name exactly as it will appear on photo ID, along with a birth date. These are airline rules, not just something Expedia or any other travel vendor imposes. So, for example, if you use the name Cindy with your friends and you book your flight using that name, but Cinderella is the name on your passport, you could be turned away at the airport for an incorrect name and not allowed to get on the plane. TSA is funny like that and not in a ha-ha kind of way.