We were, I think, the 3rd or 4th company to sign onto Truckmate when it first came out. Our server at the time was an 8088 !!! Randall Burrell's demo system took up two suitcases !!!
It has gone thru a lot of changes since then. Now owned by Trimble it is vertically integrated with Peoplenet and PCMiler, and Synergy (I think), among others.
Truckmate is scale-able to whatever size you are, or want to be. The system is really about what you want to get out of it. If you're okay with how much you made at the end of the week, it will do that. If you want to know what the exact cost is to run a given 1 mile piece of road between Chicago and Green Bay, it will tell you that as well. As with all computer programs, regardless of who you partner with, just remember, garbage in, garbage out.
While lowmiler88 is right about an ROI, it's not an ROI like you would buy a truck where once it's paid for you either sell it or run it until the wheels fall off. A TMS (transportation management software) system is really the lifeblood of your company. You're in this for the long term. The hardware will change, and software requires upgrades. You should expect that after your initial cost is paid down, you will need to spend on hardware refreshes and software support. You should probably budget for about $40k a year (again depending on size) to start with.
Whatever you do, do not cheap out on your server. Take into account exactly what you need today. Add in what your expansion plan is over the next 3 years. Then quadruple the size of your server. Virtualize everything! It's a way better environment to work in than physical installs on physical servers and desktops.
My recommendations:
1) If you do not have in-house IT, contract an IT company. I use Next Dimension.
2) Designate someone from your organization to champion your software selection. Understand this will be their primary job. Spend the money to send them for training. All they can get, and more.
3) You will need to have basic knowledge of Crystal reports.
4) You will need to know, or at least not be scared of, SQL.
5) Go and see someone's live system.
6) Lastly, if you are going with Truckmate, hire an outside Truckmate adviser.