Ask a Bougie Chick - Supportive or Enabling?

It's been a while, let's catch up on some Ask a Bougie Chick questions, shall we?

Hey Chele,
Hope all's going well with the book writing, I wasn't sure you still blogged a lot or answered these but here goes. I'm 32, biracial sister, degreed working in corporate America successfully  I own a small condo and a small car and I'd say I'm pretty drama-free. I'm also in a two year relationship with a guy who is 28. He doesn't exactly have a substance abuse problem but he definitely is a habitual user of pot and alcohol which are not so serious. 
Anyway, my overall problem with him is that I feel like I have to constantly push and prod him to take the next steps in his life. I helped him get his degree. I nagged him to get a place of his own. I nagged him to attend church regularly. I nagged him to get a promotion at work. I have him spending time with his child from a relationship previous to ours. I feel like with drive and focus, he's a really great guy. He has the smarts and the looks to go a long way. 
I don't mind providing the motivation for him professionally but how hard do I have to push to get him to solidly commit to me? I guess I'm like everyone else - I want the ring. besides dragging him to a jeweler  pointing at what I want and assuming he takes the hint - what more can I do? 
And now my friends and family are saying that I'm carrying too much of the water in this relationship and if I'm doing it now, I'll do it forever. But I think he's his own man and can stand on his own feet. what do you and bougieland think I should do next?
Thanks - CJH in Chicago
CJH - Hey girl. First let me step out of the shade of your first sentence. ;-) Next, let me insert a graphic here:

Okay, now that that is settled. I have more questions than answers. When you say he doesn't "exactly" have a substance abuse problem, all manner of red flags started waving in the wind. Secondly, you say he's a great guy but what is great about him that you haven't ooched and scooched him into? His job, his home, his church, his degree, his fatherhood? What is he showing you that you haven't shared about him standing on his own two feet? 

On the one hand, looks like you've taken some "raw material" (smart and cute) and molded and glazed it up into what you want. Good on you, you should surely reap the rewards (if there are any to be had) for basically raising a man for yourself. Is that harsh? 

On the other hand, wouldn't it be great to see what he can do on his own? If you take two steps back from pushing him up Mt. Olympus, aren't you curious to know if he reaches a hand back to take you with him for the rest of the climb? If he takes a step forward or falls back down without you? Are you supporting this man or enabling him? If he knows you'll always put the pieces together, why should he even bother opening the box of Legos?

As for the marriage part, again - it sounds like part of a master plan you have for your life that you've keyholed this dude into. Step one, get a degree  Step two, get a good job. Step three, get a condo. Step four, get a church-going man with a degree and a roof of his own. Step five, marry that man...

I'm not condemning  I once had that same list at the ready myself. However, life is longer and more complex than a to-do list. My recommendation is to fall back and see what happens when you're not in the driver's seat steering and navigating every step of the journey. Just my two cents.

BougieLand, whatcha got for CJH? Do share...