I'm comfortable working at heights, but then again I've got a lot of safety gear and training to do it correctly. Not everyone is. Getting hurt on a ladder is a high risk. Dropping tools, having the mast fall and hurt you, someone else, or your home should all be concerns. If you have any doubts about your capabilities to do this, then it's a good idea to consider either hiring someone to do the work for you, or renting the proper equipment. No amount of hobby fun should come at the cost of a dead/injured Indie. Your family would not be amused.
Safety gear and proper tools for doing this sort of stuff is —always— a good investment. While dropping a few hundred bucks on a rental lift, it's a lot cheaper than ending up in the hospital. Falls from 30 feet up don't end well. In tower climbing school we were taught that anything over 6 feet can kill.
Hard to tell from the photos, but there may be other ways to do this. Not sure what your roof pitch is like, but going up on the roof might be a safe approach. Either way, taking the mast down, installing your antenna !!!properly waterproofing the connections!!! and routing coax is going to serve you better in the long run. Trying to do all that while balanced on top of the ladder is probably not going to lead to the best results.