Walter, it's hard to answer your question, it makes more questions.
Here are a few.
1.  What frequencies do you want to operate?
2.  What modes do you intend to operate on those frequencies?
3.  What are your antenna possibilities?
4.  How much audio feedback do you want from your radio?
5.  Do you intend to run the radio in to an amplifier?

Personally, I'd lean toward the newest technology, because it should be more 
advanced.  If VHF and above are important, and you are only buying one 
radio, then the ts-590 won't meet your needs.
If you are serious about operating CW, I think the ts-590 has more options. 
If your environment is noisey, same for the ts-590.
Maybe a ts-480 plus a ts-tmv71 would work if VHF and UHF FM is important.
If satellite work is a part of your plan, then the ts-2000 is probably it.
So you see, your question creates many more questions.

H T Kaufman MSW LCSW
Adaptive Technology Instructor