Don't think that most the guys on this forum don't have the same problem. After all, this is a self-improvement website, so 99% of the users on here either
1. Need improvement
or
2. Needed improvement and have improved, and thus have chosen to give advice (the smaller majority)
You need to fight on two fronts here.
First of all you aren't confident in your lifestyle and your success. However, you know that you can achieve all these things if you put your mind to it. By knowing you can do this (convincing yourself), you will drive yourself to do it. Whether it's being successful with women, money, people, etc. If you build up enough drive to do these things, you WILL achieve them. The people who are NOT successful are always the ones building these challenges up to be IMPOSSIBLE, while all the meanwhile they are well within mine and your reach.
Second of all, you need to stop worrying about all these expectations when dealing with women and others. What you are not now, you cannot control. What you will be in the future, you can control. Tell people you have expectations for yourself. Tell them that you have big things in your sights for the future. Confirm to yourself that you are in the process of becoming something bigger. Just because you don't have material objects going for you now, doesn't mean you don't have the mental drive for all these things.
Have you been out to the clubs lately? Most the guys picking up hot women DON'T have a solid base. They may act like they do, but really you know they are most likely putting on an act.
You don't need to put on an act. Instead of acting, you are projecting yourself to what you want to and WILL be.
My friends always ask me when I go out, "Why do you act such a big role when you are still a college student living in a 2 bedroom apartment?"
My answer to this is.. Your expectations of your self eventually mold you into what you are. The self-fulfilling prophecy. If you can't imagine yourself as something bigger, then there is no way in hell you can be something bigger. As long as you are working towards this goal, acting the part is not a crime. It's a starting point.
By your post I can tell you want to be something bigger. Start prepping yourself for the part and working your ass off in the process. Like I said, it's a 2 headed front.
As far as the women go, you don't need cars and money to attract them. Be your own man, make your own decisions, and flirt with women. I promise you that you will have no problems laying women if you stick to these rules.