CAD Questions

Gentlemen:

I am not very familiar with CAD. I made a shape with a series of
lines and arc segments (36 total)using TurboCad (Ver 6) and
DeltaCad. To handle the cutter comp, it took me maybe 30 minutes
with DeltaCad and the finished product seemed OK. With TurboCad, I
couldn't get the offset correct on arcs, but spent a lot more time.
My questions are:

1.Does one have to offset *each* segment, then add the corner radii
in order to generate the compensated shape, or should the CAD do it
more or less automatically once the direction and starting point are
set?

2. Once the basic shape is completed, how long should it take to
generate the compensated shape?

3. I haven't yet tried the Ace Conveter; how should one set start and
direction of cut?

4. Since my applications are just hobby type, are there some low cost
CAD systems which you would recommend?

Thanks in advance,
Jack C.