G'day Nuke Dukem,
It depends on where you see yourself WRT aviation. If you see yourself left seat with a major airline, I hate to say it, it probably won't work. If regionals are your thing, then it's feasible (caveat - check historical hiring). Bizjets might appeal more - it depends on home life stability and so on.
So I would think about where you see yourself in 10 years time, ie 57 and what your goals are. If you can do it all and still be debt free, great. I would research the hiring practices of where you see yourself. eg have they historically taken older low houred pilots etc. The US does have the 1500 hour rule too.
You still have a couple of years to assess the plan too. Oh - find out what the Class 1 medical requirements are and see if you meet them. You don't necessarily need to do the medical, just ask your local doc to assess you on X parameters.
Any way, you seem to have given it some sensible thought. Good luck.