Yeah, but if OP listened to you and contributed 11%, they'd have made an excess contribution that they'd have to deal with.

The IRA contribution limit is $6500 for 2023, so it may not be possible to save 11% into a Roth.

Try a different software, but I would NOT recommend TurboTax. They're a bit of a smarmy company and have been in trouble more than once for leading people to believe they can file their return for free, and then telling them after they've entered all or most of their info that they have to pay to file-- sometimes when they could have declined paying and still filed for free.

When you enter a 1099-INT, the only info you need to include is the payer's name (typically the name of your bank) and the amount of interest they paid you (and any other values that are $ amounts if it's not a 1099-INT from a bank). You typically don't need to include federal or state ID numbers.

A couple things:

1. since you're talking about them not filing since around 2016, you'll need to check the filing thresholds for each year and compare their income to those thresholds to determine if they should have been filing. (You can find these in the 1040 instructions for each year. For 2018-2021, they're probably fine if they only had SS and minimal other income because the standard deduction increased substantially in 2018 and has been increasing since then.
2. They may want to file 2020 and 2021 tax returns if they didn't get the stimulus checks. Most SS recipients did, though, so this may not be necessary.

Don't repurchase the same or substantially identical security in the Roth. If you do, you will trigger the wash sale and not be able to realize the losses.

That is a downside, but not the "only" potential downside.

It definitely does, and you can effectively lose the losses if you repurchase the shares in an IRA (Roth or Traditional).

>and they earned less than $4200 in the year.

It's not relevant to u/mudra311 since they were married at the end of the year, but the $4200 income limit doesn't have to be *earned* income and the limit is indexed each year. For 2021 it was $4300; for 2022 it's $4400.

If it doesn't, it should allow rollover from the after-tax Trad-401k to the Roth 401k.

Does solo401k.com support in-service rollovers from the 401k to an IRA? Some solo-401k providers do, and some don't.

>2. My HDHP through my employer has the option to cover two or more people, but my wife and I elected to choose the "Employee Only" version of the HDHP plan we signed up under, as it was cheaper for my wife to have her own HDHP through the Health Insurance Marketplace and for me to have a HDHP through my employer.

It's important to realize that your spouse is only eligible for ACA subsidies for Marketplace insurance, if your cost for your employer's plan to cover both of you was more than 9.5% of your family's AGI. https://www.cbpp.org/blog/more-families-will-spend-less-on-health-care-premiums-thanks-to-a-fix-for-the-family-glitch

u/ShimonaLisa, Its-a-write-off is correct.

As a cash advance:

1. they get charged the cash advance fee,
2. they start accruing interest right away, and
3. they don't earn any points or other rewards.

So, what you're proposing isn't really a good idea, and it's definitely not going to be "free."