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.

Quote from @Kate Stoermer: I just did an optimization analysis of a 3 bedroom in Pigeon Forge area in a resort (shared amenities) for a client. 

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.

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. 

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.)

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?

In the meantime, I’ve heard some hosts are getting traction by leaning more on direct bookings, optimizing titles/descriptions with fresh keywords, and boosting visibility through social media.

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.

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.

Quote from @Russell Roberts: Based on continued learning and all of the generous input (I may do a paid engagement with one of you), here's the REVISED tax optimization idea.1) Direct buy multifamily property and hands-on renovate/manage for minimum 500 hrs.