Treasuries usually have better rates and are exempt from state income tax, but other than the effective return you can consider them to be the same thing as CDs, so select the one with the better return.

You buy Treasury Bills at a discount to their $100 face value, and they get redeemed by the Treasury for $100 on the maturity date. If you buy them at a brokerage, you can sell them early for market price, which may or may not be attractive. In that way they are similar to CDs - you get a guaranteed return if you hold them to maturity and can cash out early for a potential small penalty.

"Laddering" as a concept applies equally to Treasuries or CDs - the idea is to have a "ladder" of them which mature at regular intervals, meaning that you more frequently have access to cash via a maturity event, so you can access the cash without having to sell a Treasury or break a CD.

You should check the withholding rate on your commissions. Chances are that it is exactly 22%.

If your other wages are at least $109,225 (2023, Married filing separately) then this rate is too low. You need to add additional withholding to the regular checks to make up for the shortfall. The IRS calculator may be able to help.

Based on the size of your shortfall, you also need to make sure that your filing status on W-4 is Single or Married filing separately, or if it is joint that you take an adjustment for the other job in the household.

>At a 5.5% interest rate - why is 15% of my monthly payment going to interest? Why shouldn't it be... 5.5%?

Because you're not paying down the loan in a single year.

Consider the following cases:

• You pay the loan in full the day after you buy the car. You would pay effectively no interest regardless of your rate, because you didn't keep the loan very long (there might be some minimum duration or something). Your interest would be almost none of the amount you pay, or
• You never pay off the balance of the loan, paying "interest only" and keeping the loan balance the same (this is common in business loans). 100% of your payments would be interest, again regardless of the rate.

When you pay off the loan in a fixed time period, it's somewhere between these two extremes. The interest rate is the percentage of the balance that is charged as interest - if the outstanding principal is $10,000 and your rate is 5.5% then $550 of interest will be charged on an annual basis. The amount of principal you pay in addition the interest is calculated in an amortization schedule in order to both:

• Keep your payments the same amount every month, even though the amount of interest accrued each month will shrink as the balance goes down (you'll note that the interest portion of your payment shrinks each month), and
• Pay off the loan in a certain number of months

>The coupon is 0 and the current yield is a dash (-) but Ask Yield to worst and Maturity is 4.472%. Does that mean that you will get 4.742% return on the 6 months for the treasury bill?

Treasury Bills are zero coupon, which means that they do not pay interest.

However, you normally purchase them at a discount to their face value (redemption value). In this case, you can pay $97.752 for a $100 Bill that matures on June 29, 2023. You pay $97.752 now and the Treasury pays you $100 in June.

This $2.248 of profit in six months is equivalent to a 4.742% annual yield. There is no catch - this is the going rate for the US Treasury to borrow $100 from you for six months.

If the check was deposited into an individual account in his name (not an exempt trust like an IRA, Section 529 account, etc.) then it is his money, free and clear, and is indistinguishable for tax purposes from any other money he may have.

Any tax consequences that may or may not have been due the grandfather for giving his grandson that money were incurred when the check went into an ordinary account, and in that year.

Any plausible tax issue would derive from whether he spent that amount on education in that year. It's moot now.

A check is simply a written authorization of a transfer from the account number of the check. To the degree that all bank transfers are recorded by banks, they are "trackable".

You need to learn a lot more information about what is going on here, in particular on what account this check is drawing. Also, as a general note, surprise depositing a check 5 years after it is written without talking to the account owner is, at a minimum, terrible etiquette. Many banks may refuse to honor a check that is more than 180 days old.

No. FICA is 7.65% of your first $147,000 of wages paid by that employer - since it's applied as a flat tax it is representative of the gross pay on the current check.

The most common cause of this would be receiving a taxable fringe benefit or other non-cash compensation item, which adds to your taxable wages for withholding but not the cash paid.

I think that is saying that they won't permit you to ACATS the shares in-kind to another broker, so that they can no longer track them for tax purposes. There is interplay because selling the shares generates ordinary income which is customarily reported on your W-2.

I would not be concerned about a minimum holding period until a specific policy is actually announced. It's normal not to have one.

There is something more complicated about your pay than you are letting on.

Your FICA wage base for this check is $5,040.64 (figured as Social Security divided by 6.2% or Medicare divided by 1.45%), implying that your gross compensation is actually even higher than that, since your insurance contributions (health, etc.) are a Section 125 deduction and subtract from your FICA wage base.

Moreover, "Voluntary Disability" is certainly not a normal line-item in that amount, so I am wondering if it represents something other than a standard CA VPDI contribution.

Also, your federal withholding is too high for even your FICA wage base, which would suggest you did not complete your Form W-4 accurately (you don't say what withholding you requested).

>I assume the risk of the company stock dropping >15% during that administrative delay is very low then?

Generally yes. Obviously anything is possible, but it is very unlikely - especially if (as ought to be the case) your company is not reporting earnings during those few days.

>I want to confirm that immediately selling ESPP is always going to be profitable (or almost always, since I'm assuming I will have to manually sell on Etrade when I get the stock granted to me?).

Yes. As you note, the only technical risk is the few business days between exercise and practical receipt of the shares.

>My parents were saying that the taxes on the gain isn't worth it, but I'm not understanding their argument. Even if I get taxed at a high rate on the short term gain, I'll still end up making money since I got a 15% discount?

Also correct. The discount is ordinary income, on which you would never pay a 100% tax.

>Does this mean that if the company stock goes up throughout the offering period, I will still only be purchasing stock at the value of the enrollment date and making even more money, even if I sell the shares as soon as I get them?

Yes. This is usually called a "lookback" provision.

>Will there be any lag between me getting the shares on the "exercise date" and being able to sell them?

Only an administrative delay. Varies by plan custodian but it is usually 1-5 business days. The shares are delivered "as soon as practicable" but you will have a few days of at-risk time.