I'm glad you don't mind my novels!
Sounds like a pretty fun set up you and your mom will have!
I personally don't insure my project horses because I need to make a profit off of them. The more you put into them, the less money you're going to make. If I lease them out I have the leaser pay for it, regardless of the cost of the horse, so it's still no money coming out of my own pocket but if anything should happen my investment is still covered.
Do you have any good local shows nearby? With a green horse you're going to want to take them to as many places as you can. The thing about the rated shows is that they're so darn expensive. And again, the more money you put in, the less you're going to get out! Entry fees alone cost me about $5-600 a show for one hunter division, possibly without warm up classes. Entry fees at our local shows (B shows) are about $150. They still get the show environment, all the local people get to see the horse go around, and my area has a few state H/J Show associations that accrue points. The way ours work is that for every ribbon they get in that division that year, they get a certain number of points. Then at the end of the year they get ranked and awarded ribbons and prizes. Their points don't stick with them for life, but I can say, this horse was Year End Champion in 2010 in the .95 M or something. As a buyer I'm not that impressed if a horse was champion at one show, but if he's year end champion of the state? Well, that means he did ok! The more wins you can get on record the better! The downside to showing at all the local stuff is that if you have an extremely competitive horse they may not have the classes you want to enter in, and they may not draw the audience you'll want to market the horse to. The question for me is also, what caliber the horse is. If the horse is going to be a super fancy A rated horse, I'll make the investment. That's the audience I want to market that horse to. They won't care if he's champion at a local show. If he qualifies for Indoors? They'll take him more seriously. One of the ponies I just sold was good as gold, but not super fancy. I didn't waste my money doing the rated stuff but took him to tons of local stuff.
"Green" is kind of an ambiguous word in the show world depending on what division you're talking about. Usually it means he hasn't jumped a certain height. And it's usually for a hunter. If I were to show my Baby Green horse in a 3" class? I can no longer show him in the Baby Green division. He broke his green status and no longer elligable. So I'm careful when I move my hunters up because you can't always move them back down. Moving a horse up is really up to you and what your goals are. LIke I said, I wanted to try for a year end award with that baby green horse last year and he's not for sale. So I kept him showing at that height all year long. Now he has a record of being successful in that division. But the jumper I was talking about? I didn't care as much about his record. But I wanted him to have proof of doing well in a higher class and didn't want to waste time in the lower classes just for a year end award. So I moved him up. He's for sale and I can market him as a 3"6 horse because he has proof of doing well at that height. If I had kept him at 2"6 all year it would be hard to sell him as a 3"6 horse because people want proof that he can do what I'm selling him as. Does that make sense?
For rated shows the horse has to have a recording number with USEF. You just pay it once and they're in. The rider has to pay a yearly membership. I think it's around $120 a year.
There's another novel for ya!