Welcome Bob.
If you have the time to learn something new than yes it will be worth it.
A quick answer to your questions would be to get a 15" x 15" or larger Hix or Stahl's heat press. I would suggest the Heat Master that I own, but to be honest, they are currently having some problems with a few of them and some bugs need to be worked out, so hold off on a Heat Master press until further notice, even though they are very well made.
For a cutter, also known as a plotter, you will want to get a 24" wide model.
Smaller models are not as good or practical even though they will do the job. It's like buying a smaller press, they work but they are not the best choice.
The Summa D60 has always received great reviews from everybody in the industry. Others to look at would be Graphtek and Roland. Both are well respected brands. I'd stay away from the sign supply store private label type cutters. They are usually re-branded cheap cutters. They work, but they are noisy and don't track very well, and tech support is usually terrible. Also I would not recommend the Stika cutters either. They are very good, but very small and geared toward the hobbyist in my opinion.
You just might be able to squeeze a top quality 24" cutter and heat press into the high end of your budget, maybe add another $500.
As far as software, most of the time the software that comes with a cutter is what they call a bridge program. In other words it is the program that is in between your design software and the cutter. You design in your software, like Illustrator of CorelDraw for example, and then you send the design to the "bridge" program. The bridge program converts your design into something the cutter can understand. It also gives you more options for working with the layout of the cut, the quantity, the blade pressure, the material size, weeding borders, color cut, registration marks etc. There are many of these programs out there that are bundled with a new cutter purchase. I wish I could tell you which one is best. CoCut is highly recommended, but not always necessary.
Visit
www.signs101.com to learn a lot more about cutters/plotters and bridge software.