Oh boy! What a great first post. Welcome to the forum. I’ll respond with my initial thoughts but, I also think it would be helpful to know the year of your boat, your experience level as well as, how many times you’ve raised the mast and, how those experiences went. I often “trailer sailed” my first 1974 C-22 and never once had an issue raising the mast. I was 47 years younger and the pre-1976 mast was lighter, a combination that made mast raising on pre - 1976 boats easy peasy. Fastforward to today and on my 1988 sporting a heavier OEM mast, I found I need to employ an A frame, bridles on the port and starboard sides as well as the trailer winch to get the mast up. In the several times I’ve raised the mast on Waffle House, I have bent the step bolt once and subsequently replaced it. This was done without unstepping the mast, only removing the old bolt and installing the new Replacement bolt. The step-bolt IMO is a sacrificial part to help keep the mast in alignment when it is being raised. I cannot imagine a situation where the receiver hole in the mast is elongated. I would not enlarge it until we know more about your specific situation. Once the mast is raised, there should be zero stress on the mast step bolt and its connection to the mast step plate.
George
