Ok, so the MAC's in the screenshots were not from the jails? I thought they were.
So we'll round it up like this: your ISP-appliance sucks (already knew that, all ISP-appliances do :D). The root cause appears to be that you set up jail IP's within the DHCP range of the ISP-appliance, which made it choke (as all these crappy ISP-appliances do :)).
Those are DHCP reservations. Different implementations either want them outside the normal DHCP range or inside said range. In any case, they're dynamic IPs set by DHCP - they're just reserved on the DHCP server.
Yeah as I said, this is the new router. I can throw dd-wrt or whatever on it in the future if I need to. It seems pretty good so far. The problem seems to be that the old ISP router had no problem with static IPs in DHCP range but this one didn't allow it.
Although some devices allow it and others don't, in general, it is always wise to keep static IP's outside of the DHCP range. On my home network, I start the DHCP range on my router at 50 (xxx.xxx.xxx.50). That gives a lot of room for static IP's, and you are unlikely to need more than 200 DHCP allocations.
Whether or not reserved IP's work reliably will be dependent upon the router - and has been pointed out already, most ISP routers are not very good. I tend to avoid them for that reason. Your ASUS router is an excellent device, and ASUS firmware is pretty good (the Merlin builds are a little better.) You don't have to bother with DD-WRT on that box unless you need a specific feature only available in DD-WRT.