Also talk to your CPA about the impact of ObamaCare on the medical insurance side of your question. If you have enough savings/investments you can reduce your modified adjusted gross income (line 37 on your 1040 plus interest from municipal bonds)to a point where you can get substantial federal tax credits to reduce you medical insurance premium. A reduction to a level that I would consider to be "reasonable". Especially given that you only have two years until you hit the Medicare age.
