Bob,

I think you should start taking lessons. You are a perfect business flyer
that can benefit from GA.

You will likely want to start small and work up. This means continuing to
pay someone else for the longer flights. For the price you are wanting to
invest, you can't buy much plane.

Here are some issues you will run into.

How mechanical are you? If you want to own and operate an older (cheaper)
plane, you will want to be able to take care of little things yourself in a
pinch. The older the plane, the more it pays to be able to pitch in instead
of depending completely on an AP.

How is the weather? The longer the trip, the more chance of running into
adverse weather that can only be overcome by more training, more plane, and
more equipment (or waiting it out).

How flexible are you? If you are limiting your budget so low, you WILL end
up with travel issues that require spending an extra night.

I would think icing is an issue for you. Boots or TKS are not available on
your budget.

So, the bottom line advice I would give you is to start taking lessons, and
see how much you like flying. After you get hooked, and start meeting other
pilots in your area, you may want to spend more. Also,you may find a
partnership arrangement that can allow you to buy a more capable airplane.
That is likely to be your best bet.