Any other creative strategies for optimizing cash flow in a situation like this?

With your background in engineering and lean construction, you’re positioned well to optimize real estate projects, especially in a Midwest market like Indiana.

@Nicholas Martinez This is a smart question, and you're not alone—many house hackers with construction experience wonder how to optimize tax benefits by involving an LLC.

If we were to develop both lots at the same time, we may be able to optimize costs and potentially make more on our investment.

LTRs offer stability, while STRs can produce higher returns, but come with more risk and management needs.STR Tax Advantage: If you materially participate (100+ hours and more than anyone else), you can qualify for the STR loophole, allowing bonus depreciation to offset W-2 income, without needing full REPS status.Use Cost Segregation: Ask your CPA about doing a cost seg study to accelerate depreciation, especially if 100% bonus depreciation returns in 2025.Backup Options: If managing real estate feels overwhelming, consider a Delaware Statutory Trust (DST) for a passive 1031 route, or an installment sale to spread the tax burden over time.Meet with your CPA and 1031 intermediary to ensure your reinvestment strategy is tax-optimized and aligns with your comfort level on risk and management.This post does not create a CPA-Client relationship.

Proactive tax planning helps you leverage deductions, choose optimal structures, and keep more of what you earn.

If I were starting from scratch I would buy a primary with an ADU or walk out basement, and do a 1 bedroom optimized for 1-2 people. 

IMO there are two kinds of bad deals, deals that are actually bad, they make no sense on paper but blind optimism and likely relying on the wrong professionals carries you through to the closing table.

Hi all,I’ve been managing short and mid-term rentals in San Diego for several years, working closely with individual homeowners to help them optimize their property performance.

I have tried asking it about more complex stuff like portfolio design and how to optimize equity growth and cashflow and it totally fails.