Alrighty longtimefan (and anyone else who gives a hoot)---a little follow up.
My workouts have been going as planned and I have dropped 16 pounds since my last post in here (June 9th). So from 286 (very bad weight) down to 270 and I am continuing to drop hopefully down to 250. My first attempt at running a 40 was a 4.9 (at 286 pounds) and my speed and cardio is only going upwards. Strength is not an issue and won't become one.
As far as training goes, I am on my own with that but I am doing very well. I lift 4 times a week (monday, tuesday, thursday, friday) and I run 5 days a week (Wednesday I actually do ball drills and run routes).
My friend is getting his license and will be representing me come January when all the pro days begin. He told me to leave all of that to him so I am going to. I trust him as much as he trusts me (I will be his first legit client).