karillon,
nice to see fellow ex service types on the forum. Like you I served 22 years (RN Aircraft Engineer). I finished my time in January 2007, used my resettlement to get my ppl and my gratuity money to pay for hours building, CPL and MEIR, making maximum use of ELC grants along the way.
I seem to have qualified at a very depressed time for the employment market.....d'oh. I suppose I fired out about 70 or so cvs and got a few sniffs but no job offer (I don't think that being 42 years old was a factor but with current legislation they will never let on).
After 6 months in the wilderness I had to start earning some cash (my wife was very insistent) so I am working as a consultant on a 6 month engineering contract. But I will keep the faith and keep my ratings up to date in the hope that things will improve.
As far as paying to fly or paying for a type rating goes, I would budget for it and if you land a job without having to pay for one then you will be in profit. None of us know when the industry will recover and whether it will make a full recovery and the fact that you are prepared to finance your type rating may influence an operator to take you on.
Hopefully when you are ready to qualify the employment situation will be improved but whatever you choose to do I sincerely wish you every success.
Best Regards
MM