All Forum Posts by: Ashish Acharya

@Jordan Swift 

Hey Jordan, welcome!

You've gotten some great advice above. I really liked what Ryan said about buying the primary residence, living in it for 1-3 years and converting it to a rental. This is how many people find success in scaling without breaking the bank on high lending fees with investor loans.

It sounds like you've got a lot of experience managing risk with your farm equipment hobby, which is a great mindset to bring into real estate. From a tax perspective, starting with STR or mid-term rentals near college towns can be a great opportunity because these types of properties can create opportunities to offset income in ways that more traditional investments might not.

One key thing to consider early is how your rental income interacts with your current income; some strategies, like actively participating in your rentals, can allow you to offset non-passive income with losses from your properties. This helps many investors save on taxes and then use that money to reinvest in their next one. On the other hand, if you plan to keep it more hands-off, understanding the passive activity rules is critical so you can structure your investments in a way that maximizes deductions.

Happy to connect and excited to see your journey unfold!

This post does not create a CPA-client relationship. The information contained in this post is not to be relied upon. Readers are advised to seek professional advice.

@Glen Fitzmaurice 

Hey Glen, welcome!

It sounds like you’ve built a great business, which gives you a solid foundation to dive into real estate. You probably already have a sense of this from running your business and owning commercial properties, but one thing that can really influence how successful your strategy is understanding how all your income streams work together from a tax perspective, especially as you plan for retirement. 

Things like depreciation on rental units (especially now that 100% bonus depreciation is back), deductions for improvements, and how you structure financing can all impact cash flow and long-term returns. Even if you don’t need income for the next 3–5 years, thinking about taxes now can make each step of your plan more efficient and help your retirement goals come together more smoothly.

This post does not create a CPA-client relationship. The information contained in this post is not to be relied upon. Readers are advised to seek professional advice.

@Rick Ellsberry

Welcome to the community! I'm a big reader as well. I'm sure we've read some of the same books. They get you excited for the possibilities out there, and you should be excited because there are opportunities out there, especially with your background and knowledge. As a loan officer, you should be off to a great start.

One thing that can make a huge difference is keeping the tax side in mind, especially when implementing strategies like BRRRR, long-distance investing, and even planning for retirement to ensure everything is set up properly. Thinking about taxes early on can help set you up for a smoother retirement and make your investment decisions much clearer.

Looking forward to following your journey!

This post does not create a CPA-client relationship. The information contained in this post is not to be relied upon. Readers are advised to seek professional advice.

@Jason Crowe 

Great question, @Jason Crowe! I see this thread was from 20+ days ago, but I wanted to add from a business-owner perspective, virtual assistants can be very valuable. I know firsthand because we outsource various aspects of our work at my firm. That said, how you set them up makes a big difference.

From a tax standpoint, if they’re classified as independent contractors, their costs are typically deductible as business expenses, but it’s important to ensure everything is properly documented, especially if they’re international.

Like some people have mentioned above, virtual assistants can sometimes be inconsistent or non-responsive. That said, with the right setup, they can work well.

As others have mentioned, virtual assistants can sometimes be inconsistent or non-responsive. With the right setup, however, they can be highly effective.

Some of our clients have even found that hiring a dedicated full-time team member, particularly for finance, bookkeeping, or marketing, offers better control, simpler expense tracking, and more long-term stability, especially when it comes to tax planning.

Each approach has its pros and cons, but the key is aligning it with your business structure and overall tax strategy.

Happy to connect if you want to know more

This post does not create a CPA-client relationship. The information contained in this post is not to be relied upon. Readers are advised to seek professional advice.

@Zach Joyce

Great points here! Most people get into real estate because of the opportunities to create extra income; buying and then selling, as well as renting, is a big part of that. Renting can be a smart move, especially if you’re upgrading to your next home. New investors should take note: you don’t always have to jump straight into a new investment loan, which can come with higher interest rates, stricter underwriting, and more hoops to jump through. Renting allows you to start building your portfolio without over-leveraging.

From a tax perspective, there are "advantages", like you mentioned, but it’s important to understand how the rental will work with the income you are already making. How passive versus non-passive income works when turning a property into a rental. Short-term rentals can be treated differently from long-term rentals, which affects how deductions, depreciation, and losses apply. With the right structure, you can offset income, save on taxes, and reinvest more effectively.

Thanks for putting this out there! Definitely gave some people who are struggling to sell right now new ideas to think about.

This post does not create a CPA-client relationship. The information contained in this post is not to be relied upon. Readers are advised to seek professional advice.

@Susan Hsiao

Putting your short-term rental (STR) deed into your LLC can improve liability protection by aligning ownership and operations, but it comes with trade-offs. In North Carolina, lenders may have "due on sale" clauses allowing them to call your loan due if you transfer the title without approval. Check for possible transfer taxes, title insurance updates, or insurance changes. There's no change in income tax treatment, as you'll still report income and expenses the same way. Avoid creating a spousal LLC unless advised by your attorney or CPA, since it can require a separate partnership return. Many STR owners keep the property in their name, run income and contracts through the LLC, and use umbrella insurance for simpler protection. If you decide to transfer the deed, consult a real estate attorney and CPA to ensure it's done properly without triggering legal or lending issues.

This post does not create a CPA-client relationship. The information contained in this post is not to be relied upon. Readers are advised to seek professional advice.

@Bill Black

That’s exciting! A duplex is a smart way to get started. You’ll gain firsthand experience as a landlord while offsetting your own living costs. Feeling your way through is totally normal; every first investment has a learning curve.

You probably already know this, but one thing many first-time duplex owners miss is how home office rules can apply if you manage the property yourself. Even just keeping records, scheduling tenants, or handling repairs from a dedicated space at home could let you deduct a portion of your home expenses. It’s a small move that can add up over time and set you up for future success.

Also, as you get more comfortable, take time to understand Real Estate Professional Status (REPS), Short-Term Rental (STR), and Active Participation rules. These can make a huge difference in how much of your rental income and even your W-2 or business income you can offset with property losses and deductions while house hacking your duplex.

Good luck, and if you’d like to chat about how to set this up for maximum tax efficiency, we’d be happy to connect.

This post does not create a CPA-client relationship. The information contained in this post is not to be relied upon. Readers are advised to seek professional advice.

@Christopher Rubio 

I’ll explain it more from a tax perspective. The main thing is tracking your costs properly. Rehab expenses that add value or extend the life of the property get capitalized and depreciated, while true repairs can be deducted right away. Any carrying costs before the property is rented usually need to be capitalized too. When you refinance, it’s not taxable income, but you’ll want to keep your basis straight for depreciation and when you eventually sell. Clean records from the start will save you a lot of headaches later.

Understand the REPS, STR loophole, and Active participation tax rules so that you can save taxes.

This post does not create a CPA-client relationship. The information contained in this post is not to be relied upon. Readers are advised to seek professional advice.

@Yusuke Koike

@Yusuke KoikeIf you use your Illinois LLC, you can do it, but you'd need to register it as a foreign LLC in Texas and keep up with their reporting rules. A lot of people just set up a Texas LLC instead since the property and any legal matters are already in that state. Either way, the income still ends up on your federal return, you'll just have to file in Texas if your gross income is in millions (probably not applicable to you right now).

This post does not create a CPA-client relationship. The information contained in this post is not to be relied upon. Readers are advised to seek professional advice.

@Hunter Emond

From a tax perspective, financing the roof doesn’t hurt you directly — the cost is treated as a capital improvement, which means you’ll recover it over time through depreciation. The part that might affect you is the lender side. If you finance the $41k through the contractor, that new debt shows up on your credit and gets factored into your debt-to-income ratio when you go for the next loan.

So for taxes, no issue, it adds basis and future depreciation. For lending, yes, it could reduce your borrowing capacity depending on your overall profile. Some investors in your spot will look at pulling equity through a cash-out refi or HELOC instead, since that can sometimes be viewed more favorably by lenders and still gives you the same tax treatment.

This post does not create a CPA-client relationship. The information contained in this post is not to be relied upon. Readers are advised to seek professional advice