You no doubt have substantial background that will help you compared to some people starting with SDR fresh with no radio or technical knowledge.
Let's work on establishing some goals, so then we can come up with a good bill of materials.
To simply "see what's out there," any RTL dongle calibrated properly will work using RTL_Power. I am not sure what similar software is available for SDRs with higher bandwidths. You can then start exploring the active frequencies.
If you just want to search, one SDR using SDR# and DSD+ or FMP24 and DSD+ will open a lot of doors to digital, like the DMR you seem interested in and other supported digital formats.
If there are local systems you want to scan, monitor, or record, then we can get more specific and advising you. Some people want to monitor P25 Phase 2 but don't say so and then are mad when they can't on Windows, for instance. So that's why I'm trying to figure out what you want to or might want to accomplish.
The nice thing about SDR is that you can generally build as you go, and it sounds like you already have equipment. Your computers selection should be quite versatile. Loading Linux on one of them will give you ultimate flexibility.
Besides cost, the main considerations for selecting a SDR would be reliability and frequency accuracy (and stability). Sensitivity, too, but I'm not sure any of the reasonably priced ones excel substantially in that area. If using multi-dongle approaches, having dongles that have stable frequency accuracy around 0ppm eliminates some issues with getting everything sorted out in some software programs, like DSD.
You also mention that you like listening to the airband. Are you interested in communications radio only, or would you like to get into more diverse SDR projects? For example, are you wanting to collect airplane location data?
The SDR field is huge. Heck, you can almost get lost. So, if you don't have anything specific in mind or some particular major goal, I suggest starting small and cheap. Get a $10-20 dongle and see if you like it. Then go from there.