In answer to your general questions:
Loss of licence cover pays out an insured sum if you lose your licence through no fault of your own. It is a lump sum payout and like most insurance comes with a whole raft of qualifying criteria. Given that it is assured that you will ultimately lose your licence the premiums rise with age.
Pension deals reflect the general economy. Final salary pension schemes are almost extinct for new entrants. Money purchase schemes are the norm and as in the wider economy they vary from employer to employer. Employer schemes in the U.K. might typically comprise an employer contribution of 7-10% of your basic salary together with your own voluntary contributions to the tax allowable annual and lifetime limits. Remember that retirement in this profession is currently compulsory at age 65 (and medical standards may force an earlier effective retirement age). State pension age is rising in the near term to 66 and 67. It is very likely this will increase over the coming years. This can place a particular importance on the retirement planning for professional pilots.
I am in my late "fifties" I did my command course at age 28. I last went through a new type rating course (from Boeing to Airbus) 3 years ago. I cannot say I find it it difficult to pass the sim checks, because I know what is expected and apply the necessary learning criteria to maintain the required standards. Importantly, I can also balance a great deal of relevant past experience to whatever the current requirements demand. The new cadets come from intensive learning backgrounds. They are on a steep learning curve, and their keenness, application and determination most definetaly keeps you on your toes. Again, it is an aspect where relevant experience provides a weighted counterbalance. Almost all of the cadets I see are from an integrated and full time training background. Pilots from other training backgrounds are likely to have worked their way up through stepping stone jobs, and likely other airlines. Experience in those roles, together with determination, application and a healthy dose of luck, should ordinarily provide for a good pilot, They are however significantly different career paths.
If any of my children truly wanted an aviation career (one has) then yes I would encourage them to fulfill that path. Not to "follow me" because that path is long trodden and a lot of it no longer exists. They would have to tread their own path and have a strong appreciation and understanding of the realities involved.