But one extra BRRRR/year here is worth ~$75k in forced equity—so if self-managing costs me even one deal annually, I’ve over-optimized the P&L and under-optimized the balance sheet.

One of the books I've read that I'd recommend if you haven't already: The Multifamily Millionaire Volume I: Achieve Financial Freedom by Investing in Small Multifamily Real Estate by Brian Murray and Brandon Turner.

What are you trying to achieve, when, and how much work do you want to put into it?

Not something that you can optimize on your own, without a tax professional.

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.

We’re finding that investors who focus on quality locations, strategic rehabs, and strong tenant screening are still able to achieve solid returns, even if the numbers don’t look like they did a few years ago.We’ve also seen more investors diversify strategies BRRRRs, seller financing, and selective flips to keep deals working in today’s rate environment.

There are certainly a lot of benefits that the OBBA brings to MA residents who are looking to acquire a STR.The first conversation you want to have with your accountant is what you need to do to treat the property as active instead of passive(if that is what you are looking to achieve).The other benefit of the OBBA is the increased ability to write off state and local taxes as part of the itemized deduction.Best of luck to you in your search!

I could also potentially pull $100K instead and try to still do a owner occ loan and get a $5,361 monthly.I'm unsure of my goals now as it really was to achieve financial freedom with semi-active/passive income build-up but the thought of being able to leverage the cash is very intriguing to me.

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.

It all depends on your expectations; do you have a number or percentage profit you are trying to achieve?