I am 51 I unfortunately can't go back to my 25 year career (firefighter) injured in line.of.duty and getting pension out in a few months. Getting work comp settlement ok amount. My thought: become a commercial pilot don't need to be a captain or flying in the big airlines. Just need decent pay health insurance and I love flying. So is this a good thing to do? I have a few flight schools near me and I was also thinking of seeing if I can pass the medical first before paying for the program. Thanks for any suggestions or input.

Get your class 1 medical. I believe age cut off for commercial flying is 65. There's time, but after years of training,  not too much time. So do it now.

ETA: Do your licensing as accelerated as you possibly / safely can.

Unfortunately this is probably an unrealistic goal. There's little in the way of decent pay or health insurance outside of Part 121 (airline) and larger Part 135 (charter) operations. To get those job opportunities you'll burn through $50K to $100K of your savings, depending on the breaks, and 2-3 years of your life. Then you've got to compete for a position.

There's no age limit for Part 135 two pilot operations but both pilots can not be over age 65. Part 135 single pilot op's are limited to age 60. Part 121 op's are limited to age 65.

Career advice aside, doing the medical application on your own can be costly and time consuming if you get denied. Join aopa or another aeromedical service and give them all your records to see if you will have any problems obtaining a class 1 medical.

121 airlines yes, part 135 charter not necessarily. Plenty of paying gigs including PIC over 65. NetJets for example just implemented an age 70 mandatory retirement but that’s purely internal to NetJets.

On medical many AMEs will do a consultation- basically go through an exam without it being official. Would let you know where you stand

I would recommend you go for it.

Get your medical.  See what class you would qualify for.  You can settle for a Class 3, that will allow you to fly recreationally.  That won't feed you, but it will make you happy while you look for/do something else.  Once you get a class medical, you can re-up it with Basic Med, a simplified medical you can do with your PMD.

When you get you settlement, please see a financial planner/investment advisor.  I have seen hundreds of these settlements disappear with some turbo diesel dually pickups and big screen TVs.  That is money intended to replace/supplement your earnings.

You're in Illinois.  Plenty of regional airlines flying out of Chicago.  They'll provide health care and start at $90K a year.  Upgrade to Captain is practically mandatory once you reach 1000 hours part 121 time.  It pays $140k+ a year now at a minimum.  Plenty of career changers hired at the regionals in their 50s and 60s.  Downside is the absolutely crummy retirement contributions the first 10 years.

The settlement money is being allocated in two different things: high yield Cds which will be laddered, and two roth IRAs, and still have enough to pay for flight school. I ain't blowing all my $ on dumbshit, Ive honestly never been like that. Iam also pretty lucky because my old man was a CFO for At&t and a CPA so Iam pretty covered in the investments of my settlement. Iam also getting my pension at 65% of my pay for the rest of my life, which is tax free. So money wise if I make something to boost my income and get health benefits and do something I enjoy that's the goal, if I can...which today I called an FAA medical examiner office and the nurse said that I may be able to have a "physical" under my insurance with the Dr first and he can give me an opinion on which part I would be able to attain. He is under my primary cares office, so she kinda said there are some creative ways to see which class I might be able to attain with my injury. She has to run it by the DR and should be getting back to me by Thursday. I will let you all know. Thanks again for all the advice I appreciate it, seriously. Ive been trying to figure out what I am going to do.

This answer all starts with figuring out if you can get a medical.  No medical means no flying...

I know a good number of ex-military pilots who are 100% disabled according to the VA - but VA disability math is kind of crazy.

Well I talked.to the Dr who is also a private pilot, and I am filling out the medExpress and going from there. I also have 2 flight schools lined up to talk to.

The Feds have been coming down hard on vets who are getting VA disability and not reporting that on their medicals. Be careful and do not withhold any information about your disability claim that might come back to bite you in the ass.

Thank you for the heads up and will not be withholding any information about my disability to any one during this process. Really appreciate advice like this thanks again.

If your taking prescription meds be very careful what you tell the FAA. Double check what meds are allowed and what meds will cause a problem for you. Trust me I know, it got so aggravating dealing with the FAA I finally said fuck it.

Currently I have my pain being managed after nerve ablation so I actually don't take anything other than over the counter Motrin. But thanks for the heads up I will keep that in mind.

Update: well as usual lol plans don't always go the way you want. Looks like I might have to get another surgery on my back this time a fusion from L4 to S1. So we will see what happens, kinda disappointed but see what the MRI shows and the back doctor say.