Wild Card Questions
Declaring disabled son as dependent
My son’s oldest son is on disability. He turned 18 In June of last year and graduated with his class..
Help Please
I am A single mother who is only income is disabilities . Destitute I made a mistake taking a sum..
Tax free gifts to children
can I give money to my children that can be tax free?
401k Plan Smells “Fishy”!
My employer offers a 401k plan that is pooled with the entire office. It is managed by his advisors in..
Car Purchase Before Year-End
I am wondering if you can provide more info on the benefit to buying a car before 2020. We wouldn’t..
Investment in Bread Route
Hello Terry, what is your opinion on bread routes? I am looking to buy one as an investment. Also, do..
Home owners insurance
I live in a tear down. My lot is worth more than the house. A claim would require me to..
Senior citizen investment
Where should a 90 year old man invest?
Stock for grandchildren
Is it a good idea to buy stock for grandchildren I been buying stock for there birthdays since they were..
Cryptocurrency Future
Now that the IRS has included a question about virtual currency activities do you think there will be more federal..
The next bubble?
The year 2000 gave us the dot.com bubble, 2007/2008 gave us the Mortgage Crisis bubble..With stock markets at record highs,..
stock options as a benefit
Can you explain the potential value of stock options when working for a start-up? I have to be employed for..
Social security benefits for spouse
My wife is a retired CPS teacher. I am a union carpenter thinking about future benefits moving forward. When I..
Current bank safety
Hi Terry, I enjoy your regular appearances on the WGN morning program. I notice that the Federal Reserve has been..
Govt Pension reduces Social Security
My social security is greatly reduced because I have a pension with the city of CHICAGO. Is it possible to..
Medicare Open Enrollment Comment
I read your article about Medicare Open Enrollment. Most people sign up for Medicare when they turn age 65 even..
Disability & medicare
I’m disabled & have been on disability since 2005 (have MS). I was always covered thru my husbande’s ins. through..
Medicare Part D Plans change prices mid-year?
I have had the experience of selecting a Part D plan and then finding out with my first prescription in..
Medicare Medigap coverage — tough choices, need help!
I will be 80 years old in July and my husband 83 in June of 2020. We have comprehensive coverage..
Medicare enrollment — Part A
You mention in recent article that if you are age 65 and still working, you don’t have to enroll in..