@Simon ********
dont overthink things. Many of the questions are worded in such a way that suggests they want deep meaningful info. They dont, they just want to know you have accomodation and can afford to fund yourself whilst there. When i did my multi entry TR visa last year, i think i supplied pretty much the same info for 3 or 4 of the questions without any issues. Any problems and they will email you.
I even did a multi entry TR application for a friend and they gave him a 1 year non immigrant O over 50 visa without any questions about insurance. The UK embassy is pretty easy to work with.