Listen: The bottomline is that in order for you to not get "shredded" as indie calls it, you should look after yourself and not assume the best of him until he's proved he is good (too soon for that yet.) Particularily when he doesn't see you on weekends, he has a history of being in codependent and dysfunctional relationships that he is currently not yet come to terms with and he is only known to you for two weeks. You don't know him. It's okay to ASSUME that he is good if there is zero red flags but, there are red flags (more than what you've revealed more than likely) so don't be naive. It's not about taking a positive or negative slant anyway... it's about the evidence before us and how you should, if you love yourself, be weighing all this.
You don't have to be cautious and you can be positive from the get go if there are no red flags. So worrying about being a bitter old hag doesn't even have to come into the equation. This is about this guy and what you've told us about him thus far. What WILL turn you into a bitter old hag is being burnt by guys over and over again because you do not take into consideration the negative aspects of the guys that you are interacting with. Common sense tells you that he has been in an abusive relationship where he stayed long enough to show scars from it. That indicates that he has some very deep seated issues that you've yet to see rear their ugly head. Keep that in mind about him.
As for working every weekend. It's not the fact that he works every weekend that's not a problem in itself (if you don't mind being alone on those days that is) the problem is that people who are already in a relationship save weekends for their Significant other and usually are never (or very, very seldom) available for the one on the side during that time. That is what is meant by another red flag. It doesn't necessaritly mean he is married, but when you don't know him well, you should wonder if he may be. It's also a red flag because it could mean that he has other woman as well as you and he rotates his time between you and them. Hence the "when I get some free time you and I will go away together" that's often code for "when its your turn, we'll go away then." Since you don't know him well and he refused to be exclusive with you that possibility exists.. something to keep in mind as you continue on.
You assume that what I say is "baseless" but if you opened your eyes to what we've been saying, you'd understand what could be going on here. Tis better to be safe then end up being played. If you're anything like our friend (who is much older than you and should know better) you will feel awfully stupid (amongst many other negative emotions) when/if you do realize where (using 20/20 hindsight) the red flags were and when you ignored your gut.
As for asking your mother. I find that someone close to you can sometimes see things better than strangers over the internet and when they know you and your personality, they can sometimes give you a better slant on things. That's what she has to do with it. Do you not confide in your mother ever? I'm old and I still wish I had her to run things by once and awhile. Unfortunately she's not alive anymore to do so...