ah, yes...getting the binder on and off...Soon, you will be proficient in "The Binder Dance".
No, it won't combine completely, since, well, you've still got something under there. Nothing will make your chest look flatter than an actual flat chest. But getting most of the way flat while saving for top surgery money is pretty nice. Have you tried it with a sports bra?
Yes, binders are meant to bind comfortably. This is the healthy way to bind. You are not meant to feel pain, like you would with the Ace bandage approach. Now, aren't you glad we all yelled at you?:D
Get well soon, Tom.