I would not worry about negotiating with carrier and agents right now. Starting out I would rely on my dispatcher while you learn their system. Some of them are pretty good at CRST Malone. If you live around Tennessee I could suggest a place that might rent you a trailer. It is difficult to rent a trailer starting out without a track record. Most want to see some financial history or a big deposit. You can rent a trailer from CRST Malone. If it were me I would probably just get a trailer from them. It will be much easier starting out. If you go to orientation in Birmingham, there are a couple of trailer dealers who might rent you a trailer if you want to go to an outside source. If your credit is good you may consider just buying one after a couple of months if that is what you want. The advantage you have buying your tarps, etc., from CRST Malone is that they will finance it for you. I know of one guy who bought all his equipment on ebay. He got a really good deal. It comes down to how much cash you have on hand. If you have good credit and cash then you can get a much better deal.
You are not required to have a maintenance account with CRST Malone, but it is available. Personally, I would keep my own maintenance account. You will be required to have an escrow account. Again, they will make weekly deductions until the escrow is fully funded. You are required to have bobtail insurance, but you don't have to get it through CRST Malone. It may be less expensive to do so. OOIDA has bobtail insurance for members. You will also be required to have either workers comp or an occupational accident policy. I would go with the occupational accident policy. It is less expensive. OOIDA has it for about $140/month. You are required to purchase your own base plates. They will get them for you through the state of Illinois. You can probably get them cheaper through your own state, but if they get them they will finance them for you and deduct a fixed amount each week. These are pretty common for all carriers.