Man, this thread hits home.
I also plan to retire in about 2 years. The 5BW purchase was definitely part of the plan. I realized that 2 specialized cars weren't nearly as good as one great car that I could enjoy every time I went anywhere. So I went the other direction.
When I bought the Caddy, the loan payoff coincided with my retirement plans, but I think I can get away with that extra year.
All my kids have finished college. My wife has been retired for 3 years already. Every day I'm at work I feel like its such a waste of time. We're in better health now than we likely ever will be, so I constantly regret not doing it sooner. I can afford it, just wanted to avoid the 10% tax penalty for dipping into IRAs before you're 59 1/2. That last 1/2 year age requirement is so ridiculous. Seriously ? I've been working for 40 years and I have to wait 6 more months ?!?!?
Health benefits at work are great too. Unfortunately or fortunately - depends on how you look at it - I've had more health benefits paid than I've had salary for the last 2 or 3 years.
I did a cursory look at the government health insurance site, and it looked like about $1,500 for us as a couple. My wife can get it as a retiree for about the same price, but not sure about coverage details yet.