1: Gen4 on J1... Sucks compared to #3, but, if you had Ultra, you can't get any better...
2: Gen5 on J1... Still going to have slow speed issues till the load on J1 is reduced and more people switch to the HT2000w on J1.
3: Gen5 on J2... AMAZING~!!! Granted, that's because this is a brand new bird and it's going to take awhile to be fully loaded...
The *only* cons with going to Gen5 on Jupiter Two is the lease fee is $5 more per month, and the router is an all new design which means it probably has a few growing pains. This is the first time Hughes has really pushed for a router/modem combo unit. Plus, the OLD Gen4 Ultra beats anything Gen5 can offer, data allowance wise.
The pros with going to Gen5 on Jupiter Two, better speeds - for now. I suspect the mid-west where Jupiter One isn't available will be fully loaded much sooner than the areas where J1 and J2 can tag-team. You do get much higher speeds, and MUCH higher uploads for once! Hughes has been working hard on the router firmware in the HT2000W as well. We can change DNS settings, DHCP settings, modify the wifi settings or even disable wifi completely. They have even made it possible to change the LAN side IP addressing. It is an almost, full fledged router. They also include basic parental controls and website filtering options with in the modem, as well as time tables to block websites at certain times. So don't want kids or anyone hitting youtube at 6PM till 8PM for homework time? You can bet ya! Kids also wont be able to easily change that as you can password protect the router side of the unit.
As far as plans go though... I can't really help you there... All the new Gen5 plans have the same Upto speeds, the ONLY differences are data allowances. If budget is a concern I would probably stick with the plan that is closest in price. If budget wasn't too much of a concern, and you really could use a lot more data, maybe consider a higher tier plan? Just because you order Gen5 on J2 and get into a new 2-year contract, doesn't mean you are locked to the plan you sign up with. You can always change that should the need arise.
EDIT////
Looking at things, if you are on the Prime plan with 10/50GB the plan appears to be $59.99, but there are no $59.99 plans on Gen5... You might be able to go for the 20GB plan but that's $69.99/month it appears, plus the more expensive lease fee, the bright side is, it appears to be $49.99/month for the first 12 months, but I don't think anyone can get that promo price on an upgrade. You may have to call to see about what is available as far as your options go... But to me it looks like, "Spend a little more to double your daytime allowance or save $5 and keep the same data allowance".
EDIT///
ALL of that aside, I plan on doing a review of the unit sometime in next week and compare it to a Gen4 system in the review... For now you can see some on-going automated speedtests between my Gen4 and Gen5 systems, I used Identifiers on the tests to help show which is which, both units are being tested side by side, started the tests at the same time, but as is you can see how far out of sync they are because of how slow the Gen4 unit is. Even this early in the day it's slow as can be for some reason.
http://testmy.net/quickstats/C0RR0SIVE