Good luck and I think you will be just fine. If you want inspiration, there is plenty of it on here to go around. And there have been people who have repaired and brought back rigs from the dead with plenty of posts and pics to give you insight on ways to save money or make a better than original repair.
One of the best examples is Westend, and his cowboy hilton project. Not a direct comparison to your Winny, but some great ideas here.
http://forums.trailerlife.com/Index.cfm/fuseaction/thread/tid/25707172/srt/pa/pging/1/page/1
Just poke around here and learn all you can. I'm one of those who have to get others to do my repair work as I would make it worse if I tried, and I'm ok with that, understand that and can afford that route, LOL.
A man has to know his limitations! Good luck, go Air Force and keep us posted with pictures and updates!