Good questions. Personally, I would opt for the test cycle, but if you wanted to start out on a 6-8 wk Dbol cycle, you will make some progress with that. I don't think it is going to be a bad thing, just not my personal suggestion. My first cycle was Dbol only for 4 or 6 wks. I gained a ton, most of it being water weight haha. I did gain a few keepable lbs though and was happy. Then I did a test cyp cycle with 400mg and I blew up. It was a totally different experience.
I'm glad to hear that you have had some lab work done and I'm a little concerned about your natural levels. I find that guys with weak test production usually have a harder time recovering after their cycles. At your age, you're going to find it hard to find a Dr that will prescribe HRT. There is a chance that your deficiency can be treated with the same meds we would use for PCT. Clomid alone may raise your natural levels. Once you go on, your natuarl production will of course go way down and it's never fun trying to recover post cycle. Especially for you, HCG on cycle would be a good idea. You can use what you have suggested, 1000iu per wk. I personally suggest 250iu 2x wk, but know guys that get on better with 500iu 2x wk. See what works for you.
So after the cycle, the best I would hope for, is to regain your natural levels as they are now...which isn't that great. There is a chance that you will require HRT in the future, bro, and the chance is probably going to be better if you decide to use gear. That being said, HRT isn't all bad. If your body isnt producing enough test to feel ok, IMO you're much better off taking a shot each week and enjoying a full and happy life.
You could always follow your buddy's advice and run the dbol. Keep the cycle shorter, maybe 6 wks. And then see how you recover from that. I'm certain that recovery time would be much easier on this cycle than on a longer cycle or a longer test cycle.