Winning at Life with Gregory Ricks

The Weekly Wrap: 08.22.20


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Mark on the Causeway has a rental property he's looking to sell. Will he have to pay taxes on the gains from the sale? Gregory explains it balances out between the gain from the cost basis, minus what you've put into the house, and how much it's been depreciated on previous years' tax filings.

Mark in Mandeville has been forced to retire early. Should he go ahead and turn on his Social Security early?

John in Baton Rouge wants to know how converting his IRA to a Roth IRA will affect his taxes when he retires and starts withdrawals.

Bill in Covington has an investment property he is selling for a loss. Can he use the whole loss as a write off?

Ed is Waggaman is drawing on Social Security, and his wife's benefit is hit with the Windfall Elimination Provision. Will that offset continue if he passes away?

Mina in Marrero is thinking about turning on her spousal Social Security benefit, but wants to know all the rules first.

Gregory's webinar: Wine Down with Social Security continues next week, and is a good starter lesson on when you should turn on your Social Security benefits.

Alexander in Pontchatoula has a wife that passed away 20 years ago. Can he draw a Survivor's benefit from her Social Security record?

Steve in Slidell asks how he and his wife can max out their benefits together.

Dwayne Stein of Mortgage Gumbo has some warnings for unmarried couples sharing a mortgage, and some help for those unhappy with their forbearance options.

Fletcher in Grenada has an investment property, and wants to know how/if he can write off various maintenance expenses until he sells it off.

Jeff in Houma wants Gregory's guidance on doing a Backdoor Roth IRA.

Thomas in Baton Rouge wants to know where the stock market is headed from here.

How will the market react to the election?

Charles in Metairie has a pension buyout offer after receiving pension checks for the last 20 years.

John in Lacombe wants to know how to convert his IRA to a Roth IRA.

Deborah in Biloxi lost her husband last month, and just got another check from his Social Security. Does this mean she's started her Survivor's benefit?

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Winning at Life with Gregory RicksBy Winning at Life with Gregory Ricks