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Tax & Finance

I publish illustrative scenarios prepared by my practice. The participants and conversations are fictional. These are not posts by real users, accounts of client experiences or reports of actual results.

Tax obligations, 1099-K reporting, international taxation, and financial compliance.

106 threads

IRS Audit — estimated tax penalty avoidance

by seeking_advice_tenant_CO · Feb 17

1 replies

TikTok Creator Fund tax reporting under new US entity — 1099 and W-9 questions after Oracle/Silver Lake deal

by CreatorTaxHelp · Jan 24

4 replies

Capital Gains Tax — missing 1099 from defunct exchange

by frustrated_employee_FL · Jan 11

17 replies

Day Trading Tax Treatment — estimated tax penalty avoidance

by help_me_driver_today · Jan 10

2 replies

IRS Audit — stock option exercise timing

by throwaway_creator_advice · Jan 08

No replies

Estimated Tax Payments — missing 1099 from defunct exchange

by just_curious_tenant_2024 · Jan 05

14 replies

Foreign Account Reporting — home office deduction requirements

by GigWorker_LA · Dec 26

8 replies

Day Trading Tax Treatment — Roth conversion tax planning

by worried_contractor_MA · Dec 22

10 replies

1099 Tax Issue — state tax when working remotely from different sta

by frustrated_creator_legal · Dec 08

21 replies

IRS Auditing My Cash Business — Demanding 3 Years of Bank Statements

by irs_audit_cash_biz · Dec 08

9 replies

Didn’t File FBAR for 5 Years — How Bad Is the Penalty?

by fbar_forgot_5yr · Dec 03

10 replies

Missed the 45-Day Identification Window on 1031 Exchange — Tax Bomb

by missed_1031_deadline · Nov 21

10 replies

IRS Audit — FBAR filing for offshore accounts

by frustrated_driver_2023 · Nov 17

15 replies

Day Trading Tax Treatment — capital gains on inherited property

by anon_parent_question · Nov 08

10 replies

Day Trading Tax Treatment — missing 1099 from defunct exchange

by anon_driver_question · Nov 06

15 replies

IRS Questioning My S-Corp Salary as Too Low — $40K on $300K Revenue

by scorp_salary_audit · Nov 03

8 replies

IRS Says My Side Business Is a “Hobby” — Denying $30K in Deductions

by hobby_loss_dispute · Nov 01

6 replies

Estimated Tax Payments — day trader wash sale confusion

by first_time_business_owner_2025 · Oct 24

1 replies

Lost $45K Day Trading — How Much Can I Deduct?

by daytrade_loss_deduct · Oct 13

8 replies

IRS Audit — estimated tax penalty avoidance

by first_time_seller_2026 · Sep 04

18 replies

When do I make the 475(f) mark-to-market election? First year trader

by options_grinder · Sep 04

12 replies

IRS Audit — estimated tax penalty avoidance

by RemoteWorker_EU · Aug 26

19 replies

Day Trading Tax Treatment — home office deduction requirements

by first_time_student_advice · Aug 21

18 replies

Should I set up an LLC for day trading? Hearing conflicting advice on tax benefits

by daytrader_mike23 · Aug 20

12 replies

State Tax Issue — stock option exercise timing

by confused_driver_TX · Aug 15

3 replies

Foreign Account Reporting — state tax when working remotely from different state

by seeking_advice_trader_2026 · Aug 13

13 replies

Robinhood restricted my account for pattern day trading - $18K locked, can't withdraw

by DayTrader_Restricted · Aug 12

10 replies

IRS Audit — capital gains on inherited property

by frustrated_business_owner_2023 · Aug 06

5 replies

State Tax Issue — capital gains on inherited property

by help_me_buyer_question · Aug 06

11 replies

1099 Tax Issue — estimated tax penalty avoidance

by eComm_Seller_2022 · Aug 05

5 replies

Day Trading Tax Treatment — state tax when working remotely from different sta

by confused_trader_advice · Jul 29

15 replies

Big loss year on futures — Section 1256 carryback questions

by FuturesLoss · Jul 29

10 replies

Foreign Account Reporting — state tax when working remotely from different state

by confused_contractor_OH · Jul 25

22 replies

1099 Tax Issue — FBAR filing for offshore accounts

by anon_homeowner_legal · Jul 23

No replies

IRS Audit — Roth conversion tax planning

by confused_trader_help · Jul 03

13 replies

Estimated Tax Payments — foreign tax credit calculation

by AgentBroker_TX · Jun 29

5 replies

Capital Gains Tax — foreign tax credit calculation

by confused_dev_legal · Jun 28

17 replies

Capital Gains Tax — day trader wash sale confusion

by first_time_driver_2025 · Jun 26

14 replies

Parents' Estate ~$13M — Should We Be Worried About Federal Estate Tax?

by worried_heir_CT · Jun 24

11 replies

Working Remotely From 3 States — Do I Owe Income Tax in All of Them?

by digital_nomad_taxes · Jun 06

9 replies

Day Trading Tax Treatment — capital gains on inherited property

by just_curious_dev_today · May 29

9 replies

Estimated Tax Payments — foreign tax credit calculation

by just_curious_parent_NC · May 21

14 replies

Foreign Account Reporting — foreign tax credit calculation

by need_help_buyer_legal · May 05

17 replies

Capital Gains Tax — day trader wash sale confusion

by need_help_tenant_MA · Apr 30

14 replies

Estimated Tax Payments — FBAR filing for offshore accounts

by EstatePlanner_AZ · Apr 23

18 replies

1099 Tax Issue — day trader wash sale confusion

by first_time_dev_GA · Apr 08

15 replies

IRS Audit — day trader wash sale confusion

by asking_for_friend_freelancer_question · Apr 06

4 replies

Day Trading Tax Treatment — state tax when working remotely from different sta

by RemoteWorker_EU · Mar 31

9 replies

Home office deduction worth the audit risk? W-2 employee working remotely full-time

by RemoteDev_Chris · Mar 21

14 replies

Gift Tax Annual Exclusion 2025 — $19K or $18K? Confused About Lifetime vs. Annual

by confused_grandparent · Mar 18

8 replies

IRS Audit — home office deduction requirements

by throwaway_renter_TX · Mar 01

4 replies

Day Trading Tax Treatment — day trader wash sale confusion

by frustrated_trader_MA · Feb 26

10 replies

IRS says I should have been W2 not 1099 - now I owe $18K in back taxes??

by ContractorCarla · Feb 20

8 replies

Capital Gains Tax — state tax when working remotely from different state

by desperate_creator_2022 · Feb 18

5 replies

Capital Gains Tax — state tax when working remotely from different state

by anon_business_owner_NC · Feb 02

4 replies

Estimated Tax Payments — FBAR filing for offshore accounts

by help_me_parent_WA · Jan 15

No replies

Foreign Account Reporting — estimated tax penalty avoidance

by frustrated_investor_advice · Jan 14

1 replies

Working Remotely From 4 States This Year — Do I File in All of Them?

by nomad_worker_4states · Jan 13

8 replies

Estimated Tax Payments — foreign tax credit calculation

by anon_worker_CA · Jan 07

5 replies

Foreign Account Reporting — estimated tax penalty avoidance

by AgentBroker_TX · Jan 07

15 replies

Day Trading Tax Treatment — stock option exercise timing

by frustrated_investor_MA · Dec 20

3 replies

Estimated Tax Payments — Roth conversion tax planning

by help_me_employee_today · Dec 12

24 replies

Capital Gains Tax — state tax when working remotely from different state

by confused_trader_OH · Dec 10

4 replies

Estimated Tax Payments — stock option exercise timing

by confused_driver_advice · Dec 10

14 replies

Confused about forex trading tax treatment - Section 988 vs 1256?

by ForexNewbie23 · Nov 22

10 replies

Foreign Account Reporting — estimated tax penalty avoidance

by anon_trader_CO · Oct 16

15 replies

Day Trading Tax Treatment — estimated tax penalty avoidance

by first_time_parent_today · Oct 15

5 replies

IRS Audit — stock option exercise timing

by desperate_worker_NC · Sep 10

13 replies

Estimated Tax Payments — FBAR filing for offshore accounts

by desperate_parent_2023 · Aug 23

No replies

Pattern Day Trader rules - can I avoid with a cash account?

by DayTrader_Rob · Aug 15

10 replies

State Tax Issue — day trader wash sale confusion

by newbie_seller_IL · Aug 14

14 replies

Capital Gains Tax — home office deduction requirements

by confused_tenant_2025 · Aug 11

3 replies

Capital Gains Tax — FBAR filing for offshore accounts

by desperate_business_owner_2023 · Aug 06

12 replies

1099 Tax Issue — FBAR filing for offshore accounts

by worried_buyer_GA · Aug 02

6 replies

1099 Tax Issue — FBAR filing for offshore accounts

by frustrated_trader_2022 · Jul 31

1 replies

IRS Audit — day trader wash sale confusion

by desperate_investor_help · Jul 20

12 replies

Estimated Tax Payments — day trader wash sale confusion

by RestaurantOwner_Miami · Jun 24

9 replies

Estimated Tax Payments — FBAR filing for offshore accounts

by asking_for_friend_driver_2024 · Jun 11

16 replies

Estimated Tax Payments — stock option exercise timing

by need_help_buyer_WA · May 31

21 replies

Invested in QOZ Fund 2 Years Ago — Can I Still Get Capital Gains Deferral?

by qoz_fund_investor · May 17

6 replies

State Tax Issue — stock option exercise timing

by desperate_investor_legal · Apr 26

12 replies

Day Trading Tax Treatment — missing 1099 from defunct exchange

by newbie_creator_CO · Apr 18

2 replies

Capital Gains Tax — stock option exercise timing

by confused_driver_IL · Apr 02

4 replies

IRS Audit — home office deduction requirements

by confused_dev_2025 · Mar 22

7 replies

Capital Gains Tax — FBAR filing for offshore accounts

by confused_business_owner_OH · Mar 13

5 replies

Day Trading Tax Treatment — missing 1099 from defunct exchange

by desperate_homeowner_GA · Mar 13

7 replies

Oregon Estate Tax Exemption Is Only $1M?! My Parents' House Alone Exceeds That

by PDX_StressedOut · Mar 11

12 replies

State Tax Issue — home office deduction requirements

by worried_investor_2026 · Mar 08

1 replies

Capital Gains Tax — estimated tax penalty avoidance

by throwaway_trader_GA · Jan 31

5 replies

State Tax Issue — state tax when working remotely from different sta

by anon_buyer_advice · Dec 20

9 replies

IRS Audit — estimated tax penalty avoidance

by newbie_worker_GA · Nov 13

21 replies

Capital Gains Tax — capital gains on inherited property

by desperate_employee_CA · Oct 03

1 replies

Estimated Tax Payments — foreign tax credit calculation

by worried_tenant_2023 · Sep 09

1 replies

State Tax Issue — foreign tax credit calculation

by need_help_driver_2022 · Aug 17

3 replies

Capital Gains Tax — state tax when working remotely from different state

by seeking_advice_buyer_CA · Aug 15

7 replies

1099 Tax Issue — state tax when working remotely from different sta

by help_me_student_question · Jul 17

4 replies

Foreign Account Reporting — day trader wash sale confusion

by RestaurantOwner_Miami · May 22

2 replies

State Tax Issue — day trader wash sale confusion

by HRManager_Chicago · Mar 31

4 replies

Foreign Account Reporting — day trader wash sale confusion

by TechStartup_Founder · Mar 21

5 replies

State Tax Issue — estimated tax penalty avoidance

by need_help_homeowner_legal · Dec 14

3 replies

Tax & Finance

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