I could hear your uncertainty at the end of your post. Cutting him out etc....
I'm going to wade into dangerous waters here. Because it's obvious you are making progress and I don't want to discourage you in any way, however I think you may want to look at how you handled the convo on the phone about his not paying the reimbursement to you.
Yes, he may be having financial difficulties(small or large) but it caused you to have some too!!!( Major cash flow problems, I think you said.) The question is are you just letting him off some what by not being a little more attentive to the fact that he was late in paying?
I realize you were having a good convo and you didn't want to spoil it, but you were being unfair to yourself and to him to let this opportunity to show him a change in you go by.
There are ways to bring it up casually without beating him about the ears with it.
Just an example:
"I'm sure it's a pain to have to talk about this, but I noticed you haven't deposited the reimbursed for the insurance( notice this is not personal not saying to me or for me)...if you are having some difficulty please feel free to tell me, I'd much rather know than find out when it's a bit too late to ressurect the situation.I'm trying hard to be reponsible and take care of things so I don't get in over my head. I really would be less bothered if I could be prepared for it, so just let me know if there's anything happening with you,I wouldn't want you to feel like you couldn't tell me."
This tells him you care about being responsible, you care about his problems, it shows him you are paying attention and it includes him in the solution.....
"forgetting" to bring it up on the phone because you don't want to spoil the good convo you are having is AVOIDANCE. Which if I'm not all wet, is a problem you have had in the past with him.( avoiding problems, feelings, finances etc.)
Doing what you did just shows him that nothing has changed on your part, as far as that old response goes...and he can count on you to respond in the same old, same old. Which means he can take advantage of your soft nature if he wants to. Let's face it ...he did...he didn't get the reimbursement to you....and he expected you wouldn't or hoped you wouldn't bring it up! He sure didn''t ....he kept the conversation filled with details about a computer problem.
If he truely forgot he wouldn't mind telling you he forgot! and get it to you right away.
If you say something to him It gives him a CHANCE to save face and rescue the situation too! It opens it up for him to say: "Oh, so sorry I forgot!" Or "I am having a little shortage right now, thanks for covering it!"
It gives him a chance to feel included.
If you want him to notice you are moving on, then you need to take another look at the way you respond in the same old way.
This is not a 2x4..... this is just an observation from someone whose been there, done that, and really doesn't want the T-shirt!
I was the QUEEN of avoidance! So I can see what results from this kind of behavior....
I know it's almost impossible to do sometimes...but you will be sooo much happier with the reponse you get if you don't avoid touchy, difficult, testy subjects just because the waters are calm right now....
Someone's line at the bottom of their thread was: Sailors don't learn how to be sailors in calm waters.
Much love and big hugs...keep up the good work!
ps. He was a lot more responsive when you were pursueing because you were doing all the work.
It was very flattering to him, but again it was letting him off the hook...he needs to work for this relationship too if there is going to be any thing there...
"There is no committment without involvement".
ie: People aren't going to commit to anything unless they are invloved in it and if you are doing all the work, he's not involved in it.