Welcome to the forum.
I appreciate your buddies commitment to our country and thank him for his service. I can also see that he is a good friend of yours too. I have a few of those kind of buddies too.
While I think it's honorable you wanting to restore his Cub and present it to him, I don't think it a solid idea. If you don't have the tools and lack the knowledge to do it outside of help from an internet forum, then this task is not for you. I am a professional mechanic. I have also done lots of carpentry work, plumbing, electrical work, and just about any "trade" you can think of. I have not however, spent much time as a machinist. I own a lathe, and I can use it. However, I wouldn't take on a machine project for anyone unless I was sure I could handle it on my own. If this was a project for yourself, that it didn't matter if you made some mistakes, or could live with a non-professional job... then that's one thing. But, since the machine is not yours, and admittedly don't know if you can handle fixing it on your own, I encourage you to just hire it done. It will cost you some cash yes. It will still make your friend happy, and someone will guarantee the work. (Use professional people, not "buddies".) This way, if it doesn't work as intended for a reasonable amount of time, then his wife won't hate him, and maybe you. Sorry I'm the party pooper, but I just don't think that trying to do something that you can't do on your own is a bad idea. Paying someone to do it would be better. Personally, I hate the whole notion of shows like
Overhaulin'. If someone "stole" something of mine and rebuilt it without my input as to what
I wanted.... I would be beyond pissed. Leave my sh!t to me, and if I want it fixed I'll get it fixed. But that's me. Others will be along shortly to say I'm a jerk and encourage you to do it I'm sure. This isn't what you want to hear I'm sure, but that doesn't bother me. Feel free to go get yourself a Cub and be a newbie here and we will help you along the way. Even if you decide to proceed, I'm sure you will get plenty of help. Good luck either way.