Correct me if I'm misrepresenting you but it seems to me you're only thinking about physical possession. Attachments are mental and spiritual, not just physical. Giving up everything means being willing to let go of false things that we were taught, often by people who had our best interests in mind who knew not what they were doing. To give up all you have is to honestly acknowledge to one's self that there is more out there in the world worth exploring than that which I've already experienced. To follow Christ is to go out in search of all that there is that is worth exploring. The eye of the needle parable was applicable here. If you don't take the saddle bags off of your camel, it wasn't fitting through the opening in the city walls called the eye of the needle. Your camel is your transport. Can't lose that. It needs food and water. That's inside the city. A wealthy man would have lots of possessions (attachments) in his saddlebags and would be unwilling to enter the city knowing that, if he leaves his saddlebags outside with the guards, they're going to tax if not steal outright everything he left and if the guards don't, a band of thugs will come by and overpower the guards and take it all. Christ was saying that you have to be willing to pay the price to enter the city and see what's there but the rich man will assume he knows that there is nothing in there worth experiencing and will choose to miss out. That's being non-receptive. That's antithetical to truth seeking. The world would be a much more receptive and graceful place.