Thanks once again for replies. First of MudPaint I have wrote her what my instructer had told me as she is the one who previously worked with him. We were told by her that he was an absolute gentleman and a school master as his old rider was a bit lets say 'chicken-like' she needed a generally bomb-proof pony and Chester is the result of the instructers training. He was fully vetted due to him originally being a school horse. Secondly OwnedByAli you have the same idea my friend and I had about him expecting pain which was why we were going to slowly get him used to it all again. And thirdly rascalboy we believe his saddle to be a coorect fit as once again he was a school horse however we have not yet brought him but both my friend and I work at the riding school that is selling him and we know them to have checked his saddle and everything. But thank you all for your replies obviously they are all very much appreciated. Even though Chester isn't mine yet I love him to bits.