Couple of quick comments on the Ultra. As mentioned above, you may want to see what HD says in July about the new models just for consideration.
FTF, change all the fluids and oil filter (as soon as you get it home) based on this:
Oil Suggestions For Harleys - Harley Davidson Community
Heat will be a consideration. Being in Canada, it may not be as worrisome depending on where you are gonna go. I take off my lower fairings in the Spring-Fall down here in Texas (> 37* during the day!!). But you may want to consider an oil cooler for the engine. HD's or Jagg's are easy to do.
The engine will be factory setting lean out the door. If you do high flow air cleaner and freer flowing exhaust, that will get worse. TFI is user friendly plug and play fueler that you can adjust as needed. Race tuners and other tuner type devices require more fiddling. Don't buy an HD remap. Get an adjustable option.
Depending on your stature, you may need to consider lowering the bike. If you do, go with HD stuff and do both front and rear the same amount. In any event, pack ALL the heaviest stuff first in the boxes from the bottom up. Leave the light stuff for the Tour-Pak.
I don't have one yet, but most folks rave about their back rests. If I was headed out on the road for some distance riding, I would definitely get one.
I upgraded my speakers when the HD ones tubed. Just went to Walmart (looks like they stopped carrying them) and got some Pioneers 2-way 25 Watt RMS (like these
Pioneer TS-G1342R (tsg1342r) 5-1/4" Speakers Car Speakers Car Audio and Video - Sonic Electronix). They sound much better than the original speakers.
I have changed to the REACH seat for the reasons sighted in the posts above. I personally love the seat but more importantly, I like how stable the bike now feels after lowering front & back and lowering me with the REACH. The bike is a joy to ride.
TQ