edit-First of all, Thaks guys!
Here's what I've gleaned so far:
Don't buy Chinese. This pretty much applies to everything in my life at this point. I'm tired of getting screwed.
3 Jaw chuck- PB, Bison, Gator, or TMX. Find it in Set-Tru, and with 2 piece jaws if possible. Consider a 6 jaw-hadn't thought of that, but yeah, that might be handy for making bushings and small stuff. I will also keep a weather eye out for a collet chuck.
Carbide boring bars: Probably best to E-bay this, AS NEEDED for specific projects. More info: my friend has asked if I could go into production on a small volume basis of some ~4" diameter by approx 3" tall "boxes" with screw on lids, sort of like a small jewelry box. That's my most immediate need. But I'm going to need to make bushings of all kinds of sizes for various broken farm stuff. So I will need to reach 6" deep at some point.
Taper shank drills: Yeah, I'm not buying those new! I'm watching for deals I can't turn down, but I'll grab them either cheap, or as needed.
Grinder and learn to grind HSS: I do need to do this, I understand the geometry. I have probably a lifetime supply of HSS bits from 3/16" up to 1 1/2" (that's probably going to be a parallel). I've been keeping an eye out for an old Baldor or similar, but haven't come up with one yet. I will probably have use for a D-bit grinder at some point, just not right at the moment.
Inserts: I'm likely fine with WNMG for roughing since I already have some. I do need to come up with a LH and neutral tool holder (or just use HSS for chamfers, I have some that just need honed a little). Consider DNMG for finishing stuff.
Mill: If budget was unlimited-consider Wells Index. This actually isn't off the radar. The main problem is I haven't been able to get them to return an e-mail. I may give up and just call them. I think they even have a dealer localish to me. I believe that the 847 has 40 taper as an option, but that's a big hole in a quill that size. I don't know on that one. I would probably be fine with any of the Taiwan made mills, they're all similar.
more on bridgeport style mills: I don't like the head swivel being that far behind the head. I don't know why they designed it that way. It's significantly closer to the C/L of the quill on an Wells Index, and appears to be on some of the larger Taiwan mills. I feel like this is more conducive to staying in tram. It might not really make that much difference...
Horizontal bandsaw: Check out Ellis. Good info, they were not on my radar. It doesn't look like coolant is an option on those. How's that affect the life of blades? I'm still watching for a used one too. I lost a bid on one from work that was a 5 year old 13" Kalamazoo. Dangit.
Budget: I should have maybe added some info? My immediate budget is approximately $30k. It's probably double that over the next 4 years or so. I am a huge fan on not buying stuff I don't need, so that doesn't need to get spent either. My logic is that with the way the universe is going, I would probably be best served to get the machines bought with the quickness before they get any more expensive. I'm in my early 40s here, so I'm buying with the intent of using whatever I have for the next 30 years or more. That's one reason I'm trying to find quality stuff. I also take very good care of stuff with the intent of it becoming someone else's when I croak. The machines and tooling I fully intend to be GIVEN, not sold to someone young that can/will use it when I die. I won't leave any debt that needs cleaned up, and between the property, life insurance, and my lack of a family, no one is going to need the money for it.
Used equipment: I'm near Wichita KS. I can't even explain how much machinery is stashed around here. I think Abom had a video visiting one of the warehouses down there that's literally acres of machines and tooling retired from the aircraft industry. I did NOT think to look there for bandsaws. I should do this.