First off, read this if you haven't already:

http://www.airlinepilotforums.com/fl...reer-read.html

About piloting...there are a very wide range of pilot jobs, from very crappy small-airplane jobs with crappy QOL, and pay less than $20K to very, very senior airline captain jobs which can pay $300K-ish with very good QOL.

At age 36 you will never reach the top, mandatory retirement is 65 (for airlines only , not for private commercial flying). The best you can hope for is to make a decent wage (maybe $100K) and have a decent QOL before all your hair turns grey.

RW training cost is higher, and it can be harder to get a job. Also the pay tops out lower than FW, maybe a little over $100K for the best jobs. But the good news is that there are not too many "dues paying" RW jobs, so your first job (after CFI) will probably pay enough for food and rent.

You will need an ATP license for an airline job. The realistic path to that (it requires 1500 hours) is to first get a commercial license and CFI ratings. This will mean 280-300 hours and cost $40-60K plus living expenses (you can spend a lot more, but that would be getting ripped off). Then work as a CFI to get 1500 hours (2-4 years), then apply to regional airlines.

After 1-8 years at a regional, you upgrade to Captain. After 1000-1500 hours as a captain (2-4 more years) you can reasonably expect to get a major airline job...hopefully you can stay with that airline for the rest of your career.

You will need living expense money during training. Also, due to very low pay you'll probably also need extra money during your employment as a CFI and your first year as a regional pilot.

In your shoes I would want at least $100-120K in cash to finance your entry into aviation (training and living expenses)...otherwise it will be painful or impossible. This assumes you are single with no debt, child support, or alimony. A dependent spouse and kids would make this impractical for you (on the flip side, a really understanding spouse with a really good job could subsidize your aviation career).

Assume that you'll need a 4-year college degree to get any decent aviation job unless you are very well connected (you aren't, or you wouldn't be asking these questions).

There is a theoretical possibility of a pilot shortage over the next 10-20 years...if that happens you could move up more quickly (the lower end of my estimate) and maybe get a major job without a degree.

Aviation is not going to be a solution for unemployment...you either need a good job to pay for flying, or a bunch of money. Also keep in mind that almost no flying jobs will have pensions...your retirement will be social security (which probably won't exist for you) and whatever you can save in a 401k.