Perhaps I missed the response to this somewhere along the line. In the opening post it is written “The boy I have in mind currently wants to learn in Kollel the first few years of marriage.” Is this a two way feeling or is this a little fantasy word of yours where you confuse boyfriend with serious prospective husband. Does he see you as a legitimate spouse, or are you his “girlfriend”.
You state that you see yourself as possibly being married, in college and working to support a husband and g-d willing eventually a growing family.
Are you able to physically handle being a wife, student and employee all at the same time?
Can you handle all of the above emotionally?
What expectations do you have from your spouse (whoever it might be) in this relationship, do you for example, expect help with housekeeping? Shopping? Cleaning? Laundry?
Your current boyfriend, what are his expectations from his spouse? Is he expecting to be married to supergirl who has 36 hours a day to earn a living, attend college classes and do the appropriate course work, keep a clean and neat home, and have three meals on the table ready when he is hungry? If yes, are you prepared to be that person? Forget luxuries, I am talking about basics.
Have you ever thought about these things for yourself? Have you discussed it with your long time boyfriend, now handpicked spouse to be?