Very cool with the vanity call, and great story!
Sounds good, and makes sense with the General. Definitely good to have, and will give you access to every band there is. The reason I ask about HF, is that for around double your budget, you can usually get a fairly nice radio that covers HF through UHF all in one radio on the used market. Are they the best HF radios? No. Are they the best VHF/UHF radios? No. But they give the new operators a good taste of everything ham radio has to offer, outside of DMR/Fusion/D-Star, etc.
As far as DMR, there is no quality DMR ham radio for mobile/base use, as far as I'm concerned. I personally use Motorola commercial gear for that. But they are not necessarily for the budget conscious. That said, I have picked up most of those radios for around $400-500 on the used market, but they are all single band, don't have the ease of use of being programmed from the radio itself, etc. There are a lot of limitations that you aren't going to have in an actual ham radio. But you can't beat the quality.
But here's my major concern. Seeing as you already have the 2m mobile radio and the 2m/70cm handheld, I don't think you're going to achieve anything new by getting a different 2m/70cm radio, aside from thinning out your pocketbook.
You should already be able to do everything (ouside of the digital modes and SSB, CW, and such) with the radios you already have. There aren't really any radios designed to be used as base radios anymore for strictly VHF/UHF (The IC-9700 is a notable exception, but it's also a $2000+ radio). 99.99% of the people simply use a mobile radio and power supply with external antenna, or a handheld at home. And you already have that. I would hate to see you waste $400 just to give you a different version of something you already have.
As much as people hate the Baofengs, since you have a DMR repeater nearby, you could always get another cheap handheld, like the Baofeng, to try DMR and see if you like it. If you do, you can get a better radio. If you don't, you're out $50. You could also get a hotspot and run all different digital modes using that, hooked up to your home internet. Of course, you're just talking to people over the internet that way (though many of those are talking through various repeaters throughout the world), which might not be your cup of tea. Without spending a dime, you could head over to the Brandmeister website, for example, and listen in on the various talkgroups using their hoseline. That way you can get an idea of what's out there on DMR. Of course, that's just one of the DMR networks in existence.