If you ride it continuously 2 up it won't be an issue on the BASIC RT you still have a nozzle under the seat to add air and provided the shock don't leak it will maintain it for days...The issue comes at night with headlight adjustment if you constantly switch from 1 to 2up and vise versa....even small air pumps blow the fuse for the 12v accessory in the trunk and I am not brave enough to go to a larger fuse and chance it...So.....Before a trip I air mine up to the right pressure and we just ride it 2up everywhere if it is dark out especially....And it works...
I kinda wish I had the rider floorboards and fog lights of he more expensive model, but can live without it for the $ savings....Wife and I don't need all the Bluetooth helmet crap and connectivity, We have been yelling over each others shoulders for so many years that I'm not sure we could even get used to that fancy stuff. For a simple kinda guy/gal the radio, cruise control, and rest of the stuff the stock RT has is adequate....If we had come from a Wing To a Spyder I might have opted for a SE instead, but coming from standard cruisers the amenities are abundant , to us anyhow...
Besides, If you are lacking something you find you can't life without, just get it installed....
Be patient at first, coming from 2 wheels the handling will drive you crazy if you let it, you have to learn to hold the grips loosely and gently guide the handlebars the direction you want it to go....Grip them tightly and you will be riding a rattlesnake...Takes a few hunnert miles to get used to it, and a little longer to find its sweet spot in the twisties, then you have it made....Enjoy your new experience and best of luck to ya! DC1....