What a struggle - but of course we were all beginners once (rather too long ago in my case!).
Suggestions/questions:
Do you REALLY need to have 110psi/7.5 atmospheres in the tyre? Unless you are a very hefty person then 6 atmospheres/90psi will give you a nicer ride, with a little more resilience.
When the time comes to replace tyres, think about getting 25c, again this is an easier rolling ride, and believe it or not an awful lot of tubulars used at high level are closer to 25c than 23c, for the rolling reason and the smoother ride (which counts in a 5 hour race)a
You have obviously had a lot of practice with changing tubes in 700c wheels, why not keep a few old tubes, practice patching using self adhesive patches, and then chenging tubes, when you are indoors, so if one pinches, no matter.
When fitting the tube put a little air into it BEFORE pushing it into place within the tyre, this helps prevent pinches. Push the tube firmly into the tyre and use hands/thumbs as much as possible to pop the tyre on - the more lever work the more chance of damaging the tube. Some soft beaded tyres can be pushed over the rim completely simply with strong thumbs and willpower.
And when you are confident and have a bit of experience, when replacing tubes try latex, they will lose pressure more quickly than standard tubes, and need careful fitting, but will reward with a smoother ride again, and be more puncture resistant simply because they are more flaxible. As a bonus they can take a higher pressure without loss of ride quality.
Phew! Hope this is of some help..and enjoy the riding
