1. Why is it so difficult to figure out things like cost basis when doing taxes for SPP and RSU transactions?

1a. I cant' figure out if I'm being double taxed or not with the treatment at vesting, DQ dispositions, etc of these things as ordinary income and then capital gains, etc. It's very confusing. I have a feeling I'm getting double taxed but can't figure it out.

2. Why are we limited to $3000 capital loss offset? That seems so minimal compared to potential gains and losses these days.

Yup. Taxes. Yum. That’s why I pay a guy. Not because I can’t do my taxes but because I don’t need the aggravation.

CPA does mine.
When I looked at how long it takes me and I still worry (for good reason) I may have done something wrong or left money on the table, I look at how many hours it takes me to save the fee, it's money well spent.

I use a free tax service for us older folks that is sponsored by the local library done by retired CPA's and tax consultants. Works for me.

Jim

Yup good CPA. Doesn't cost that much and well worth it.
When the IRS called to audit me this year for 2017 including years 2015 through 2019 I signed a power of attorney for my Tax guy, gave the IRS his number, told him to call me if needed and to send me a bill when done. He said oh no, no charge for audits! They aren't done yet but only one simple question from them so far.

I couldn't figure out what SPP means. But with RSU (Restricted Stock Unit), you would have gotten a statement when the stock was awarded to you and that gives you the cost basis. I was liable for taxes in the year the RSU was given me.

I've used Quicken from the beginning. And I've done my own taxes except for the first year even when I had to read all the IRS publications. That helped give me the foundation for when I started using tax software from the beginning also starting with Parsons Technology.

BUt I understand about the complexity. Sometimes, it's not worth the hassle unless you have large enough amounts. For example, I had an autobot program manage short term money and it was set to minimize taxes. It did so by investing in various muni bonds via a mutual fund. Well, some muni bonds were taxable and some not taxable as far as California is concerned. And the fund didn't give any details. I turned off option to invest in muni bonds because of that.

Use a CPA. Saves time and hassle. Life is short. If you can afford it get others to do things you do not like to do. Taxes is one. If you are ever audited you will be glad you did.

I'm also in the CPA category. I have a small business and I send him all my back up and Quickbooks stuff, a few days later he sends back my draft and we discuss further as needed.

I can't speak for the stock headache though because I just got in to the market this year, but I presume i'll get some official docs from Fidelity and I'll just forward that over to him with the rest of my papers.

SPP likely means Stock Purchase Plan. The ones I was involved with were called ESPP or Employee Stock Purchase Plan. If I recall correctly, the employee chose a percentage of their gross to be contributed to the ESPP. They ran for six months. Closing price of the company’s stock was noted on the first and last days of the plan. Whatever money the employee contributed over the six months was used to buy the stock at 85% of the lower of the two prices. If I recall correctly, any change was returned (no fractional shares). I don’t recall if it was pre- or post-tax dollars that went into the ESPP, but I’d guess it was post-tax dollars. Tax treatment would vary based on what you did with the shares.

Assuming it was post tax dollars and you held the shares long enough for long term capital gain, the simplest case would be that your basis is the amount contributed less any “change” returned and your taxable gain would be the difference between that and your net proceeds on the stock.

You should have received a statement at the closing of the plan laying out the net amount invested and the number of shares purchased.

From recollection, there was no additional tax on the 15% discount, but I may be misremembering or the rules have changed. It’s been at least seventeen years since I looked at it.

I did my taxes with Turbo Tax for quite a while, but it finally got to the point where it just wasn’t worth the time. I’ll join the chorus of folks suggesting an accountant. They have ongoing professional education to keep up with the crud that gets changed every year. I don’t have time for that even if I did have interest (I don’t have interest either).

Good luck!

Thanks guys.

I can do it (So far. At least I think I'm doing it right). But it's an annual thing so each year, I need to re-learn how to do it. And then go find the right information across various websites. And cross reference data. So it's about a 6-8 hour exercise that's somewhat stressful and painful.

Finding a CPA may be good moving forward but that's another story - not sure how to find someone I can trust, etc. I've never had a CPA before - no idea how to find a good one. It's kind of like finding a good car mechanic for me. I don't have the skills so no idea what to look for.

^^^^^^^^^^
Ask your bank branch manager. They know who handles money in your town. It worked for me. There are CPAs on this forum who could help with a referral.

for a little clarity, that $3000 limit you are talking about is a limit on losses that can be applied toward ordinary income, AFTER you have offset short and long term gains with losses that you may have. If you have more than an additional $3k in losses it will carry over to the next year's tax prep.