Comfortalbe With Purchses Made Online?

To tell you the truth, i purchased my first car online; well my parents bought it. However, i think that gives you a good idea about my comfort level with the market system on the web. EBay was the enabler of this purchase and through this system we used a secure payment plan that kept our information personal.
After few background checks of this long distance offer we were able to send a cashiers check through the mail to the dealership that was selling the car. Carfax is a firm that actually looks at the vehicle and writes a detailed description of the car including a rating from 1-10. This told us that the car was in good condition and we were being told by a firm in which we could trust. The most uncomfortable part about the situation was that the car was coming from Virginia; so in order for the car to arrive in our hometown safely we had to use dependable auto shippers to transport the bulk. This was a little scary because we were misinformed about the estimated time of arrival of the car, and we were also unsure about the condition. Turns out the car was fine and i had the best 16th birthday present i could've asked for.
Overall the purchase of the car online wasn't so bad because of all the precautions we took during the process; from the secure payment system, to the background check through a trusted company, we felt pretty comfortable with the purchase. If we changed some of the characteristics of the buying process, such as a for sale by owner, or sending the payment directly to the personal seller, the situation becomes much more uncomfortable.
Other purchases that i have made online include music, software, and clothes from large, well known companies. Clearly there is a boundary i will not cross when it comes to online buying. I wont give random sellers my personal identifiable information, unless its through a trusted company in which i am familiar with, or if much thought and research has been conducted through a questionable company. No major problems have occurred within the lines of my online purchase history, otherwise i would not be comfortable with purchsing online.