I'm really on the fence. I've got an SI joint issue from falling on my tailbone snowboarding with my son like 6-7 years ago, so seat of the pants comfort is really going to be the key. I had a Victory Vegas and loved it but sold it once I moved last summer, then got a Vstrom, and was laid off and sold that thing. I loved my Vegas and it's the only thing I ever reference for a cruiser-style bike. I'm 6'2 260, so I need forward controls obviously. These are my current considerations:
Vegas/Jackpot (bigger seat)
Raider/Warrior maybe, (Stryker seems a bit tiny)
V-Rod, early years and the only HD worth a look
Concours/VFR1200/FJR1300 (Comfort factor,ABS,etc.)
It's all a matter of comfort in the end. I know I can get a better seat on anything. My budget is ideally $9k and under, used obviously with less that 15-20k miles on it. Thoughts?
I've got personal experience with 3 of the bikes that you listed there and I have tailbone problems as well. I've owned a Raider and my brother has owned a couple of V-Rods and a Councourse 1400 (all of which I have ridden significantly). IMHO the Raider is the best big tire / factory chopper style motorcycle out there. The 113" Yamaha V-twin is the best V-twin on the market if left in factory condition. But, it will kill your tailbone (the bike actually caused my tailbone injury). I don't care how good your seat is, any bike that has your feet way out in front of you is going to put pressure on your tailbone. I tried everything to fix my tailbone issue on that bike but it just couldn't be done.
V-Rods are great motorcycles and the seating position won't put pressure on your tailbone. But, they are small motorcycles that don't feel or sit like a cruiser. I'm 6'-5" and I am very cramped on a V-Rod even with the forward controls. The early V-Rod's had tiny gas tanks (like filling up every 90 - 100 miles small). The biggest issue with V-Rods for me is the 15,000 mile valve services. They are a big pain and would prevent me from ever owning a V-Rod.
The Concourse 1400 was a hell of a motorcycle. They are faster (by a lot), handle better, stop better, and overall just do everything better than cruisers. But here is the thing, they still aren't cruisers. You can't move your feet on those bikes and eventually your knees start to hurt (at least mine does). The seating position will relieve the tailbone pain but at the expense of comfort in your legs. To put it this way. Even though the Concourse does everything better than a cruiser. My brother still sold it and bought a Victory Vision.
I'm a big fan of used Visions as the best deal out there for a motorcycle that will do everything. I know you can find them for less than $9,000 as well. You just can't get more comfort and utility for less money. I've never ridden a Vegas but if it worked for you before I'd have to say it has to be a front runner. Just looking at the seating position I think it would eventually hurt my tailbone but if you had good luck with it in the past that says a lot.
The thing that sucks about tailbone pain is that you can't just go for a test ride and determine if the bike will work for you. I have to ride a bike for several hours before I can tell if it is going to bother my tailbone or not. So you having a good history with the Vegas says a lot for me.