What tax software are you guys using for business + personal combo situations? I've been using TurboTax but it seems to get confused when I try to offset my business losses against capital gains.

One thing to keep in mind is the timing of when you can actually use those business losses. If your business is subject to the "at-risk" rules or "passive activity loss" limitations, you might not be able to use all the losses in the current tax year, even if they would otherwise offset your capital gains. Also, make sure you're properly categorizing your capital gains - long-term vs short-term makes a difference for tax rates, but both can generally be offset by ordinary business losses. Short-term capital gains are taxed as ordinary income anyway, so the offset is straightforward. Long-term gains get preferential rates, but business losses can still reduce them dollar-for-dollar. Since you mentioned significant gains and losses, you might want to consider whether it makes sense to realize additional gains or losses before year-end to optimize your tax situation. Just be careful about wash sale rules if you're thinking about selling and repurchasing similar securities.

Not sure if anyone mentioned this, but there are some exceptions to the estimated tax penalty! If your total tax minus withholding is less than $1,000, you won't face a penalty. Also, if you had no tax liability last year (a 12-month period), you can avoid penalties regardless of this year's situation. And sometimes the IRS will waive penalties for reasonable cause like natural disasters or other unusual circumstances.

Just wanted to add my experience here! I was in almost the exact same situation last year - both my spouse and I are W2 employees and we underpaid significantly. We ended up making a January 15th estimated payment, but honestly wish we had known about the W-4 strategy earlier. The January payment did help reduce our penalty, but we still owed some because the IRS calculates penalties quarterly. If you still have paychecks coming before year-end, definitely consider increasing your withholding through a new W-4 first - that's the best way to completely avoid penalties since it's treated as paid evenly throughout the year. Also, double-check if you qualify for any of the safe harbors mentioned. We found out we could have paid just 100% of our prior year's tax liability (since our AGI was under $150k) rather than trying to estimate our current year's liability, which made the calculation much simpler.

I've been dealing with a similar situation with multiple K-1s from various investment platforms. One approach that's worked well for me is using TurboTax's "Interview Mode" rather than "Forms Mode" when entering K-1s. In Interview Mode, TurboTax asks you questions about your investments and can handle multiple entries more efficiently. When you get to the partnership section, there's an option to "Add Another Partnership" that maintains context from your previous entries, so you don't have to re-enter common information like your personal details. Also, before you start entering data, I'd recommend sorting your K-1s by the boxes that contain information. Many startup K-1s only have entries in boxes 1, 11, and 20, so you can group them and enter similar ones consecutively. This reduces the mental switching between different types of entries. One last tip: TurboTax Premier has a feature called "Easy Entry" for investments that can handle multiple similar entries more efficiently than the standard interface. It's not prominently advertised, but you can access it through the investment income section.

As someone who's been through this exact nightmare with 60+ K-1s from various crowdfunding platforms, I feel your pain! Here's what finally worked for me after years of trial and error: First, upgrade to TurboTax Premier if you haven't already - the basic versions just can't handle this volume efficiently. Second, before you start entering anything, create a simple spreadsheet where you categorize all your K-1s by the types of entries they contain. Most startup K-1s follow similar patterns (ordinary income in Box 1, Section 199A info in Box 20, etc.). The game-changer for me was using TurboTax's "batch entry" approach in the partnerships section. After entering your first complete K-1, look for the "Similar to Previous" option when adding the next one. This copies the structure and you just update the amounts and company info. Also, don't overlook TurboTax's import feature for investment statements - while it doesn't work directly with Angellist CSVs, you can sometimes format your data to match what TurboTax expects for bulk import. One warning: be extra careful with your Section 199A deductions across multiple K-1s. TurboTax sometimes miscalculates these when you have many partnerships, so double-check that total manually.

This is such a complex situation! I went through something similar when I was trying to qualify as a real estate professional while my husband had rental properties managed by a company. One thing that might help - since you're getting married in April, you'll want to be extra careful about documentation starting January 1st of this year. Even though you won't be married until April, if you're filing jointly for the tax year, ALL your hours from January 1st will count toward the 750+ requirement. For your farmhouse renovation, the key is proving business intent vs. personal use. Since you plan to sell it, keep detailed records showing this was always the business plan - purchase documents, renovation budget focused on profit maximization, maybe even get a before/after appraisal to show the business value you're adding. Regarding your fiancé's rental property - the beauty of the election to treat all rental activities as one is that you don't need to materially participate in EACH property individually. Your combined hours across all real estate activities (including your renovation work) can satisfy the material participation test for the entire portfolio. Just make sure you're tracking everything contemporaneously - date, time, specific activity. I learned that lesson the hard way! Also consider whether you might qualify under the "more than half your working time" test since you're a SAHM - that could actually work in your favor here.

I've been following this thread and wanted to add some practical insights from my experience as a tax professional who frequently deals with real estate professional status claims. One critical point that hasn't been fully addressed is the timing of your marriage and how it affects your qualification. Since you're marrying in April, you'll need to be extra careful about how you structure your activities for the rest of the year. The IRS will look at your combined filing status, but they'll also scrutinize whether your real estate activities were truly "businesses" versus personal projects that became businesses after marriage for tax purposes. For your farmhouse renovation to count, you'll need to establish that it was a business from day one - not just something that became a business when you realized the tax benefits. Document everything: your business plan, market research showing why you chose this property, renovation budget focused on maximizing resale value, and keep detailed contemporaneous time logs. Regarding the 200+ unit rental property - the election to treat all rental activities as one is powerful, but be prepared for IRS scrutiny when combining a hands-off managed property with hands-on renovation work. You'll need to show some level of involvement in the rental business beyond just making the election. This could be reviewing management reports, making strategic decisions about the property, or participating in major decisions even if day-to-day management is delegated. The key is creating a clear paper trail that shows legitimate business activity, not just tax avoidance. Make sure every hour you claim is defensible and directly related to your real estate businesses.

This is a classic case of an employer misunderstanding how payroll withholding works. Your boss is conflating the standard deduction (which reduces your taxable income when you file your return) with payroll withholding requirements, but these are completely separate things. Federal income tax should be withheld from every paycheck based on your W-4 form and the IRS withholding tables - there's no "threshold" where withholding doesn't start until you earn a certain amount. The fact that you're seeing zero federal income tax withheld on your pay stub confirms your employer is handling this incorrectly. You'll want to address this quickly because if proper withholding doesn't happen throughout the year, you could face underpayment penalties when you file your taxes, even if you ultimately don't owe much. I'd recommend showing your employer the IRS Publication 15 (Employer's Tax Guide) which clearly explains withholding requirements, or having them consult with a payroll professional to get this fixed properly.

Your employer is definitely wrong about this. There's no federal tax threshold where withholding doesn't start until you earn a certain amount during the year. Federal income tax withholding should begin with your very first paycheck based on your W-4 form and the IRS withholding tables. What your boss might be confusing is the standard deduction ($14,600 for single filers in 2025), but that only affects your final tax liability when you file your return - it doesn't change the requirement to withhold taxes from each paycheck throughout the year. Since you confirmed no federal income tax is being withheld, you should definitely address this with your employer immediately. You could end up owing a significant amount at tax time, potentially with underpayment penalties. I'd suggest filling out a new W-4 form and asking your employer to start proper withholding right away. If they resist, you might need to make quarterly estimated tax payments yourself using Form 1040-ES to avoid penalties. Document everything in case you need to show the IRS later that this was an employer error, not your choice to under-withhold.