I would get the Dexter brakes. It is only an extra $100 and you can get parts for them. As far as the tongue jack, the price difference will probably less than $50 for a heavy lift jack. A heavy lift does not have to work hard to lift your TT and will last longer.
I had to adjust my brakes during our trip this summer. We only had about 1000 miles on the TT when we left. I adjusted just before leaving but decided to check them about 3000 miles into the trip. I had to do a substantial adjustment. I know that the brakes would be considered new when we left but the adjustment made a huge difference. The guy in the next campsite could not believe that I adjusted the brakes in under 15 minutes parked on my site.