@KD3PC - another one of your problems may be that your questions are pretty broad. They're not as "specific" as you think. Even when I read them, the first thing that pops into my head is, well, what exactly are you trying to do? There's a lot of software, both free and pay, that will do a lot of different things with radios in a lot of different ways. For example, what "specific" software is needed to run the latest digital modes? Off the top of my head, there are now three software packages that will do FT8. And FT8 is not the only "latest digital mode." Have you looked at their manuals? You may key in on something more specific that'll answer some questions for you. Have you looked at their web sites and found what kind of software/drivers are available for the radio you're looking at and what operating systems they are for? That, too, may answer some questions for you. Same types of things for radios that are designed to be portable and stand alone--those words alone imply they don't need the internet. On the other hand, if you're going to hook a computer to them and operate FT8, you'll need accurate time. But there are also ways to get accurate time with or without the internet. The problem from their end is that they have a very low chance of answering your question accurately and then you'll be even more frustrated. They know this and are also trying not to frustrate you. You may have better luck talking to some of your local friends, seeing what they're doing and how they're doing it. That may also lead you to ask some more "specific" questions about a particular radio.
@K7JQ, I never had a "customer service only" job in my life. My jobs in computers/communications were both technical (install/operate/maintain) AND customer service in between intalling, operating and maintaining. The only "customer service only" jobs I know of are associated with large companies, like phone carriers and internet service providers. They call it "level 1" call center service. I would venture to say it would be difficult to find a Ham Radio only company that has a position or positions of "only providing customer service." And, yes, if that's all you do and you don't do it well, or don't want to do it any more, then, yes, it's time for you to move on to something else. I moved on from the computer/communications business 13 years ago mainly because of some of the impossible customer service predicaments I was put in.
Just providing my perspective. It can be a very difficult thing to "GIVE" everything to anybody who "DEMANDS" everything be handed to them without any effort on their part. There has to be some effort from both parties if there's going to be an effective exchange of useful information. Been there. Done that. Moved on.