At the risk of getting too in-depth or confusing you with even more "advice" I wasn't going to reply, but I can't help myself! You've gotten some good information...sometimes I think it can be hard to know what to take and what to leave. I wanted to share some thoughts on a few different topics here...I'll try my best to be concise.
First, your dad...I have to respect the fact that he's your dad and probably "the boss" so I want to encourage you to think about your motives and your approach. I know he's agreed to let you AI one or two cows...you want that to pay off so this doesn't turn into an "I told you so" situation! I suggest you include him in your process so this can be a project he becomes involved in as well. When you're successful, he can be a part of that and feel successful, too. Ask his opinion and consider whatever his experience has taught him. The two of you together will probably make better decisions than either of you could on your own or by listening to everybody else you might ask. If it works out, then both of you can be proud of the results. If it doesn't work out AT FIRST, then together you can make adjustments.
Here's the short list of necessities. These are the MUST HAVES in order for you to be successful with this venture:
Facilities. Doesn't have to be fancy, but you do have to be able to catch a cow and hold her relatively still. If you don't have a head gate/working chute, put that on your list of upgrades for your program. Not only is it immensely helpful when it's time to AI, there are so many reasons every cattle operation should have one! You'll look back someday and wonder how you ever got along without it! A blocking chute will work for one or two females that are halter broke, but it won't suffice for every animal you may want to AI in the future.
Heat detection. It sounds like you have some questions, and this is an important step. At breeding time, you'll have best results if you watch for heat for at least 20 minutes in the morning and 20 minutes in the evening. You want to AI approximately 12 hours after the ONSET of STANDING HEAT...meaning once she STARTS to stand, breed her 12 hours later, even if she's still standing which some will do. Since you won't see every animal's ONSET of standing heat, a good rule is if you see her standing at the morning check, breed her that night. If she's standing at night, breed her the next morning. This is called the a.m/p.m rule and it's basic AI protocol. If you're working with somebody else who will be doing the breeding, obviously you'll have that person's schedule to work around. Just try to time it as closely to ABOUT 12 hours as you can and give that person as much notice as possible. A little advance notice and respect for other people's time and effort goes a long way! Read articles about heat detection that are printed in sire catalogs or find some online. The information is everywhere and it's a vital step. You can do everything else perfectly, and if you don't time the insemination close, it's all for nothing. It isn't HARD...just important.
To know when one is coming in, IS in, or has been in, you have to watch them. A female that's coming in will start by trying to mount other cattle. She'll usually look alert and maybe nervous. She may walk around and even bawl some. Or she may not. Look for slightly restless behavior and especially trying to mount other cattle. Also two cows standing head to head with the heads dropped down low is a sign that one is in early stage or coming into heat. Good articles on heat detection will have diagrams. When she stands to be mounted, that's "standing heat". Breed her about 12 hours later or as close to that as possible.
Semen handling and breeding technique. Find somebody and hire him or her. A class for you would be great at some point, but it's hard to get good unless you get some practice. Somebody here made it sound WAY easier than it is! It isn't hard if you know what you're doing. The first time you try it, you will think, "They must be kidding...right?" It sounds like you have enough interest in this that it's not something you would give up on easily, so just keep trying. A lot of people get pretty good at it, so there's no reason you can't be one of those people!
Sire selection. Oh...sire selection. This is huge. There are SO MANY bulls to choose from. My recommendation is not to choose your AI line up based on what everybody else is using. See every calf you can see for yourself and know as much about the program as you can that produced it. Just because somebody has success with one bull doesn't mean he works in every breeding scenario. I'm involved in breeding cattle and have been all my life. The club calf thing can get really fickle, and some bulls are a fad today and gone tomorrow. I recommend at least starting with proven sires that have a reputation for doing what you want to accomplish in your breeding program. Having those bulls available to use is a lot of the beauty of AI. Decide what you're breeding for and set some goals and some parameters. Calving ease and birth weight are important or else all the time and effort and money you've put into this canl be wasted, not to mention the hit you take emotionally from losing a calf. If you stay in the cattle business, you will lose one now and then, but losing one of your first ones is really discouraging! Especially since your dad has been reluctant to help or allow you to start AIing your cows, you want some early signs of success. A hard pull or a dead calf will not be one of those signs! Getting a calf that isn't any better than any other calf you've had born isn't going to help your cause, either! Choose your bull wisely and confidently. And again...ask your dad what he thinks about the sires you like. Including him in the selection process might prove to be a very valuable decision down the road!
Here's the thing...there is no doubt that AI has advanced the beef industry as much or more than any other management tool available. It requires more effort and more investment, but most things that matter do! If the pay-off weren't so great, the whole industry wouldn't be using it. Nutrition is important. Herd health is important. A good vaccination and mineral program is important. But nothing else you can do can move your breeding program forward as fast or as far as using AI. Any bull you want to use is available. You may not see major or noticeable improvements in one generation. In fact, depending on the bulls you've been using and the bull you choose to AI to, it's very likely you won't notice a massive shift in one generation. But set some goals and decide what your breeding program is all about...have a vision. Then make wise decisions about sire selection and the genetics you put into your cow herd. Over time, you will make progress that you cannot and will not make without utilizing AI. I promise.
My dad started AI on his herd of commercial cows in 1971. I took TWO CLASSES before I felt comfortable "practicing" on my own cows! We try to AI every female at least one time before turning her in with the clean up bull. And as far as our heifers, I like to AI them twice if I have to before turning them out. If you're making the right decisions, your youngest females should be your best, and that makes them the lifeblood of your cow herd. You mentioned calving problems, but the truth is you should have LESS calving problems because you can breed your heifers to bulls that are proven not to be a problem. Again...SIRE SELECTION! Keep in mind that performance and muscle and bone are all positively correlated to increased birth weight and increased incidence of calving problems in heifers. Choose your sires wisely!