Has anyone tried just ignoring sales tax compliance in states where you only have a few sales? What's the realistic chance of getting caught if you're a really small seller? I'm only doing about $50k in sales total across all states, with most sales in my home state.

I totally understand your frustration with the destination-based system - I went through the exact same confusion when I started my online business! The key thing that helped me wrap my head around it was realizing that sales tax is fundamentally about WHERE the consumption happens, not where the business operates. Think about it this way: if you walk into a physical store in California, you pay California sales tax regardless of whether that store's headquarters is in New York. The online world is just trying to replicate that same principle. The customer in California is using California's infrastructure (roads for delivery, legal system for consumer protection, etc.), so California gets the tax revenue. You're right that it's administratively burdensome for small businesses though. The good news is most states have "small seller exceptions" - you typically don't have to worry about collecting tax in a state until you hit either $100k+ in sales OR 200+ transactions in that state within a year. At your current volume, you might only need to register in a handful of states. I'd recommend doing a nexus analysis to see exactly which states you actually need to worry about. Many sellers think they have obligations in way more states than they actually do!

If you're tight on cash, also consider filing your taxes early but scheduling your payment(s) for later dates. You can file now in February and schedule payments for March and April. This way you know exactly what you owe but can still split up the payments. I do this every year when I owe.

Another option to consider is using the IRS payment estimator tool to double-check your calculation before making any payments. I made the mistake last year of calculating my owed amount wrong and ended up overpaying by about $200. It took months to get the refund processed! The tool is free on the IRS website and can help you verify that $850 figure is correct. It's especially helpful if you have any unusual income sources or deductions that might affect your final tax liability. Better to catch any errors now than deal with corrections later. Also, if you do end up needing more time to pay, the IRS short-term payment plan (120 days or less) doesn't have a setup fee, unlike the longer installment agreements. Just something to keep in mind as a backup option.

This is a complex situation that's worth getting right given the property value involved. One thing I'd add to the excellent advice already given - make sure you're properly documenting everything for the suspended passive losses. The IRS requires you to track these losses year by year, and with depreciation creating substantial annual losses on a $1.6M property, you'll likely be accumulating significant suspended losses. Also consider the long-term strategy here. While you can't use these losses against your dividend income now, they'll become fully deductible when you eventually sell the property. Given that you inherited it with a stepped-up basis, you might want to think about whether this property fits your overall investment strategy or if there are better alternatives. One last thought - if you're planning any major improvements to the property, make sure you understand the difference between repairs (immediately deductible) and improvements (must be depreciated over time). With depreciation already exceeding your rental income, maximizing immediate deductions through proper repair classifications could be beneficial.

I've been dealing with a similar inherited rental property situation for the past two years, so I completely understand your confusion about the passive loss rules. What everyone has explained about the passive activity limitations is spot-on - you won't be able to use those rental losses against your dividends and capital gains with your income level. One thing I wish someone had told me earlier: consider doing a cost segregation study on that $1.6M property. With such a high basis, you might be able to accelerate some of the depreciation by separating out components like flooring, fixtures, and landscaping that depreciate over 5-7 years instead of the standard 27.5 years for residential rental property. This could create even larger losses in the early years that get suspended, which means bigger deductions when you eventually sell. Also, since this is inherited property, make sure you're not missing any potential deductions for estate-related expenses or property preparation costs that might be immediately deductible rather than added to basis. The combination of high depreciation and proper expense classification can really maximize those suspended losses for future use.

One thing that helped me when I started at Liberty Tax was practicing with mock scenarios before actually sitting with clients. Ask your manager if they have practice returns you can work through. Or have friends/family bring their last year's tax documents and practice entering everything (just don't actually file them!). The software does most of the heavy lifting, but getting familiar with the workflow and where to find different sections really helps with confidence. And confidence is half the battle when you're sitting face-to-face with someone trusting you with their financial information!

I totally understand your anxiety! I worked at a Jackson Hewitt kiosk for two seasons and that first week was definitely intimidating. Here's what helped me get through it: First, don't underestimate how much the software actually guides you. It's designed for people with varying experience levels, and it will literally walk you through each section step by step. The interview questions pop up automatically based on what the client tells you. Second, most kiosk clients really do have straightforward returns - W-2s, standard deduction, maybe some education credits or child tax credit. The complex business returns and investment portfolios usually go to full-service offices, not kiosks. Third, your district manager expects you to call! I was calling mine 2-3 times a day my first week, and she told me that was totally normal. They'd rather you ask than guess wrong. One practical tip: Keep the IRS Publication 17 bookmarked on your computer. It's the comprehensive tax guide that covers almost every situation you might encounter. When something comes up that wasn't in your training, a quick search there usually gives you the answer. You're going to do great! The fact that you're already thinking ahead and asking questions shows you care about doing good work, which is honestly the most important quality for this job.

Has anyone here used QuickBooks for managing their S Corp? I'm trying to figure out if the Self-Employed version is enough or if I need to upgrade to the more expensive versions.

Great question about S Corp setup! I went through this same decision process last year. One thing I'd add to the excellent advice already given is to really think about your projected income level. The S Corp election becomes more beneficial as your profits increase, but there's definitely a threshold below which the additional complexity isn't worth it. Also, don't forget about state considerations - some states don't recognize S Corp elections or have additional fees/taxes that can impact your savings. Make sure to factor in your specific state's requirements when running the numbers. The reasonable compensation requirement is real and the IRS does audit this, so be conservative in your approach. I've found it helpful to research salary data for similar consulting roles in my area to justify my compensation level. Better to err on the side of paying slightly more in salary than to face an audit later.