Joe Anderson, CFP® and Big Al Clopine CPA answer frequently asked financial planning questions about divorce, tax deductions, business profits, Roth IRAs, IRA rollovers and more from Investopedia in episode 56 of the YMYW podcast. Original publish date August 13, 2016 (hour 1). Note that content may be outdated as rules and regulations have changed. 

00:00 - Intro

02:32 - “I am paying off a loan for CDL (commercial driver's license) school, and wondering if it is tax deductible. Does it matter if I no longer work in the trucking industry? I'm fairly inexperienced in the area of tax deductions. I understand the interest on loans is the only part that is deductible, right?”

04:11 - “After a divorce, can assets be distributed to into an account that is not in my ex-spouses name?”

06:54 - “Can a company have an extremely high gross margin and negative operating margin at the same time?”

07:58 - “Will I have to pay capital gains tax on the sale of two different homes?”

11:20 - “Can I draw $30,000 out of my ROTH IRA and put it back within a short amount of time?

12:22 - “I am a high income worker (over $250K / year). I would like to do a Roth IRA for my wife using the back door method. What would be the benefits of a Roth IRA going forward?

16:24 - “My late wife and I bought a house 20 years ago for $450,000. My wife passed away 4 years ago to cancer, so for the last 3 years I have been filing my taxes as a widow. I'm planning to sell the house for $900,000 now. How much capital gain tax am I supposed to pay? And how much tax exemption can I get?”

20:42 - “Is a 401(k) QDRO distribution taxed twice?”

28:48 - “You can wait as late as age 70 to collect Social Security, and for many of you that’s probably a really good idea because you’ll get a lot more benefit doing that.”

29:47 - “A lot of you are behind in your planning, but a lot of you have done a great job. Here’s a way to do a little self-check; there are really five things that you need to consider when it comes to financial planning.”

34:34 - “Part of being successful [in retirement] is saving on taxes because what we see is that a lot of people have the majority of their assets in retirement accounts and when you pull those dollars out, you need to pay ordinary income taxes. Here’s the key: people have a lot more control over how much they pay in taxes than they might think.”