Welcome Dave!!!
Age really isn't a factor...well until 65 anyway (for airline flying). It is possible to get all your ratings while working (I am in the process of doing that). It's cheaper at the local airport (FBO) than at the super-fast academies. This site has a plethora of information, so I would say:
1. Dig around and see what others are saying...you can see that hiring is very up and down, been that way forever and that isn't going to change.
2. Hit up the local FBO and take a discovery flight. It's usually less than $100 and you can see if it's something you might like. If you do like it (I would say there is about a 98.9% chance you will like it, and like it A LOT) then I would get rolling to get your PPL. If you fly 2 or 3 times a week you can get that done in 3-6 months.
Again, there are SO many variables in this industry, so just spend a good few (or 50) hours perusing the pages...you will find a lot of information and this will assist you in making a decision that is good for you and your family!!!
