At the end of the day, your research might ultimately reveal that neither is an optimal solution and there is another scenario that is better for you. 

My family and I recently relocated to Worcester, MA, and we’re currently operating one of our residential properties as a short-term rental (STR).I’m seeking some guidance and insight regarding tax implications and optimization strategies for STRs.

From there I was able to get into my first SFR, which my wife told me that I could no longer house hack.Along the way I was able to save much more money, and purchase investment properties throughout San Diego, both on my own, and in partnerships/syndications.Without knowing anything about your situation, I would say that buying a condo/townhome to start is going to be the optimal choice for a few reason:1.) riding the equity wave up will help when you make the move to multifamily. 2.)

By handing off maintenance to a professional team, you free up your mental bandwidth to focus on what really matters: finding your next deal, growing your portfolio, and enjoying life.For us, professional maintenance isn't just about fixing things; it's about optimizing your investment for long-term success.

A few I’ve seen work well:Targeted Google & Facebook Ads – cheaper once you know your audience.Local SEO & Google Maps optimization – people are searching “storage near me.”Referral programs – reward current renters or local businesses for leads.Dynamic pricing tools – inspired by Airbnb/STRs to optimize rates.Seems like consolidators are great for quick growth, but once you hit critical occupancy, going organic + tech is where the real margin shows.Curious if anyone is using dynamic pricing or online booking tools outside of Sparefoot?

I am quite a ways out from having enough capital to buy my first property but I would be super happy just to pick your brain and see if I can optimize my strategy to get me going in the right direction from the get go! 

It’s easy to get swept up in the thrill of sourcing and closing deals, but without a strong foundation in these areas, your growth may be at risk.An effective tax strategy helps you optimize deductions, leverage advantageous tax structures, and retain more of your earnings.

., booking management, repairs, advertising, tenant communication), as the IRS may closely scrutinize these claims.Keep supporting evidence such as receipts, invoices, emails, or calendars, which can strengthen your position.Differentiate personal use vs. rental use of the property to avoid reclassification issues.Understand potential recharacterization risks—without proper substantiation, the IRS could reclassify your STR income as passive, resulting in additional taxes, penalties, and accrued interest.Review annually with a tax advisor/EA to ensure your activities align with current regulations and to optimize deductions (e.g., depreciation, repairs vs. improvements, start-up costs).Failure to follow these requirements can significantly weaken your position in case of an audit.

To ensure correct classification, consult a real estate tax expert to optimize deductions and compliance.This post does not create a CPA-Client relationship.

A well-optimized website, active social channels, and even a simple investor newsletter can make brokers and sellers take you more seriously before you ever meet in person.Track record storytelling matters.