Hi there, Jay. Youngun' here (18), but I've been lifting since I was 14.
1.) I use fitocracy. They have an app for the ipod, ipad and iphone, as well as a web site. I recommend the site more than the app though. It is sort of like facebook, but for people who are trying to get fit and in shape. And its free.
2.) Here is what I do:
Monday: Run + Calisthenics/weights
Tuesday: Calisthenics/weights
Wednesday: Run + Calisthenics/weights
Thursday: Calisthenics/weights
Friday: Run + Calisthenics/weights
Sat + Sun: Rest
I do the couch to 5k beginners running program on my run days. Every day, I warm up by dancing/jumping around to some music. I also ride my bike on non-run days if I feel like it.
If you want to start lifting, I recommend googling "Starting Strength" or doing Sean10mm's Stripped 5x5.
3.) Now, getting a barbell would be good. But only if you used it for stuff like curls and not for pressing or squatting. Why? Because you need a spotter! People have died because they didn't have a spotter. If you want to do more, i would recommend that you that you invest in a gym membership if you can. If there is a Gold's Gym or a YMCA nearby, I would check out the prices. Golds is fairly cheap. And that way, you have people that you can ask about your form. If you aren't sure about how well you pass, or you want to wait until you are on Testosterone, that is alright, but I would definitely recommend going to a gym. Also, no Cross-fit. The worst form I have ever seen has been at Cross-fit competitions.
If you get a barbell, remember that the bar has weight too. For example, the bars we lifted in high school were 45lbs. There was a 30lb bar, we called it "the girl's bar". Misogynistic, but hey. So say you can curl 30 lbs in each hand, and you want to see if you can curl 60lb with the barbell. You would take the 45 lb bar (or whatever weight your bar is) and subtract that from 60, you would then take that number, 15lbs, and divide by 2. This gives you 7.5 lbs, or a 5lb weight and a 2.5lb weight. You would then add those on, put a clip on it, and then start lifting. These are the weights that weights usually come in, 2.5, 5, 10, 25, and 45(commonly referred to as a plate). Sometimes gyms will have 30 lb weights too. Just keep that in mind.
I'm done ranting, but that was my advice.

If you want to know more, just ask.