Best option? Direct-buy or through dealer?
Shop around.
Examine what you are using CAD for and how powerful of a program you need to put your work on paper.
There are always alternatives.
Should you want to stay with Autodesk, then your real concern will be tech support, training and installation.
Will the middle man always be there for you, if so, then get it in writing.
If not, then he is just a salesman.
0.02
I like AutoCAD. Solid and reliable.
I am just curious why this Giant sells directly, as opposed to other giants that requires customers to go through dealers.
I ask the question to the dealer: "what are the benefits of buying from you (phrased a little less direct at the time)?" It was a week ago, I haven't heard from him since. I guess I got my answer.
When I cross-graded from LDD2i to plain AutoCAD2013 the dealer was able to give me a reduced price whereas if I had bought direct from Autodesk my LDD2i wasn't considered upgrade worthy.
At the min. a dealer should offer you 1 free lunch each year for the opportunity to sell you additional products.
There should also be the option to receive un-relenting e-mails and phone messages during construction season.
Seriously though, support through Autodesk is nonexistent.
A good dealer will attend training and be able to either answer your questions or have resources at Autodesk to quickly get your answers.
Being a certified trainer is a must as it shows they are staying current.
If used sparingly, this support should be included with your purchase.
I have a local dealer that I can no longer purchase from due to Autodesk structuring. They still offer me all the support I ever received.