Joe

Since the mortgage interest is a deduction and not a credit, you will always come out ahead with a lower rate. If you are in the 28% bracket, for every $1 less interest you save, you end up with 72 cents in your pocket. I prefer to think of the mortgage interest deduction as just an additional “discount” on my interest rate.

If your insurance is through your employer, you might just want to run the numbers. In our case, our employer pays the full cost of the High Deductible plan and we use the money that a PPO would have cost us in payroll deductions, to fund our HSA. In the end, we would spend that money either way, but this way the money is ours not the insurance company’s. We are a family of 3 with no significant health problems (knock on wood). Your situation may be quite different

Be careful with how you handle that cough drop expense in your HSA. Starting in 2011, over the counter meds are no longer eligible expenses unless you have a prescription. If you can get your doctor to write an Rx for those cough drops or Tylenol, then go ahead and claim them. Otherwise, you could be in for a surprise if the IRS decides to look closely at your return.

One of the black holes in the way most people use budgeting software (including YNAB?) is they don’t account for taxes deducted from their paychecks. My approach is that I set up an account that serves as the financial “in box” for everything we receive in paychecks, interest, dividends, etc. For example, when a paycheck comes in, I enter the gross amount, then divvy out the various disbursements, including amounts to FICA and other federal taxes, state taxes, 401(k) and other retirement accounts, deductions for medical, dental, life, and other insurance. This way I can see the actual expenses for everything, rather than just “what they want you to see”. The balance on this account is always 0, but it shows me the whole picture.