Here are six questions that may help you evaluate any financial decision. Any good idea should improve your situation in some way.
Try asking these questions of your current planning strategies and see if it helps.
Will this idea help reduce my tax costs now and/or in the future?
Does it reduce or remove a risk in my financial life? Can that be measured?
Does this idea reduce expenses? Business expenses and investment expenses can really add up.
Does this increase my probability of achieving my financial goals? This is measurable by most financial planning programs. Your own planner should be able to illustrate this in some way for anything you are considering.
What is the cost of the strategy now and for the long run? Fees and expenses can add up. Make sure you are getting value for what you pay.
You should know what might go wrong with any strategy, and plan accordingly.