Originally Posted by Danny Noonan

As someone who got on with a regional at 51 and now heading to a major I can attest that age won’t be a barrier on its own. I made switch from technical side of advertising/marketing so your backstory sounds familiar.
Your additional details probably require some prep. Go get a first class medical initially to make sure there’s no gotchas. You can let it lapse into 2nd and 3rd class as you go through training. Taking loan for this career switch is a big gamble. There isn’t a guarantee that high regional paydays or hiring wave will be there by the time you have the qualifications. Make a 3-5 year financial plan with exit ramps in case you have any issues including deciding the hoop jumping for ratings and hours isn’t for you. Finally talk to as many pro pilots as you can find locally. The pro pilot schedule is very different than 9-5 M-F slog. Pluses are you don’t take work home with you. Minuses are much less control of week to week schedule and irregular hours.