Here's what I know from experience.
The new attorney in our office was the Office Manager/Legal Assistant at a law firm of 3 attorneys (2 partners, big cases - small town)for 5 years. She decided after year one to go to night school at the local law school (we don't have an ABA accredited one here, but the local one is locally respected). Two months before she graduated, they hired another attorney. Six months before she graduated, she had asked for two months of leave so she could study for her Bar. They said, "no, sorry, we'd rather just fill your position at that point". They later stated (shortly after hiring new atty) that they really didn't have room for another atty b/c they just hired one. So, she went off in search for another job with three letters of recommendation from the firm.
She landed in our office because one of the partners was opposing counsel in one of our cases. The sole practitioner (my boss) was in a depo and casually mentioned that his associates had recently left. Partner said, "hey, I know the perfect person who just took the bar but it will be three months before she finds out if she passed". There was also discussion of not hiring her on because she had worked there for 5 years, it would be hard not to have the "assistant expectations" from her even as an atty. In other words, in their eyes, she would still be support staff with a law degree.
Now, as I work for both of them now, I talk with process servers and court clerks who recognize her name and always have good things to say about her and how happy they are that she is an atty (yes, she passed the bar). During the five years of paralegaling, she mangaged to gain a good reputation here. Her prior bosses put in great words for her as she searched and she acquired a job as a result of it.
Now, my boss has discussed my staying at the firm in exchange for tuition if I go to night school. I think that's a completely different situation.
I think it's important to make contacts but not to have expectations from your current employer b/c it is always possible that you will never be looked at as an "attorney" at the firm.
I think it's possible to be offered a job but, as my current boss says, "you're very marketable because you don't need your own assistant to type or draft pleadings. You are a package deal."
My thoughts on the whole "package deal" is that it could be a trap. As an assistant, I'm already super busy. I can't imagine lawyering and doing my job.
Just some things to think about.
p.s. you are not a loser by going to night school. The atty I referenced has no student loans and has a cushy atty's salary now and works 7 hour days mon-fri.