All Forum Posts by: Jonathan Bombaci

Hey guys!

We hope to see you at our Worcester Meetup on January 15th! Come join us for drinks, apps, and learn about investing in real estate!

Best,

Jon

@Jay Hinrichs its a good question. I do know many lawyers that own investment properties themselves and in conversation have found out that most of them represent themselves in court during evictions. Maybe try to find someone like that who is just starting out and realizes that real estate is the golden goose over building their own law firm? 

This year, our management company, which oversees 700+ units in Massachusetts and New Hampshire, spent over $209,000 on attorney fees, primarily related to evictions. It’s gotten me seriously considering bringing an attorney in-house to handle evictions and other legal needs moving forward.

I’m evaluating this from two angles:

1. Cost Efficiency: With the expense as high as it is, having in-house counsel could potentially reduce costs over time. Instead of paying billable hours for every case, a salaried attorney could handle the same volume of work at a more predictable cost.
2. Service Quality: I also see an opportunity to provide better service to ourselves and the owners we represent. An in-house attorney would focus on resolving issues efficiently rather than driving up fees with extra billable hours, which can happen with outside firms.

That said, I’m questioning whether this is the best perspective. Are there risks or hidden costs I might not be considering? For example:

How well does in-house counsel adapt to different jurisdictions, especially if we’re managing properties across multiple states? What happens during periods when the demand for legal work is lower? Is the cost of retaining an in-house attorney still worth it?

Has anyone else made the leap to in-house counsel for property management or other legal needs? If so, what did you learn, both the good and the bad? I’d love to hear your experiences, especially if there were unexpected benefits or challenges.

Looking forward to your insights!

Hello Everybody,

Please join us at our next virtual meetup on January 2nd! We hope to see you virtually!

Best,

Jon

Hey guys!

We hope to see you at our Lowell Meetup on January 9th! Come join us for drinks, apps, and learn about investing in real estate!

Best,

Jon

@Michelle Wang, I completely understand your frustration, and I want to say that you are not alone in this experience. Many landlords, myself included, have faced the challenges of dealing with problematic tenants and the complexities of Massachusetts laws.

In fact, we specialize in buying properties in Massachusetts and New Hampshire that come with ongoing evictions and difficult tenant situations. What we have learned is that most people avoid these properties entirely, which allows us to purchase them at a significant discount. Over time, we have developed systems to handle these situations as effectively as possible. We have one property managers whose job is to be our eviction Laison across the whole portfolio. We approach each eviction the same way and have our playbook every time a resident gets behind on rent. 

To give you an idea of how we approach it, we assume the worst-case scenario right from the start is 9-12 months of no rent, $5,000 in legal fees, and an additional $5,000 in expenses to deal with moving their stuff, putting it in storage, and dealing with health code violations or NOV's from the city during the process. A common delay tactic is to call the board of health on a problem the tenant created themselves. In one particular circumstance we had the same tenant intentionally damage their heating system and then calling in a complaint. That said, we rarely face that full outcome. Most of the time, we resolve the situation in less than three months through cash-for-keys agreements, court mediation, or by creating enough pressure that the tenants decide to leave on thier own.

We currently manage over 700+ units and flip about 20 multifamily properties a year, the majority of which have inherited tenant problems. I can tell you that we learned these lessons the hard way, just as you are now. What you are experiencing is, unfortunately, part of the learning curve, but it can pay dividends in the future.

One of the investors who spoke at our Lowell meetup shared a similar story. He bought two four-family properties in Brockton and ended up doing seven evictions in his first year. Most people would walk away after something like that, but he used the experience to build his expertise and now owns 50+ units. The frustrations you are facing now will help you grow stronger as an investor.

Keep pushing forward. You will get through this, and while it feels overwhelming now, this chapter will one day be just a stepping stone in your real estate journey. Time has a way of healing these challenges, and the lessons you are learning will help you avoid similar situations in the future.

We’ve just finished our 2025 planning meetings for our six largest projects, and it’s been an interesting process. In terms of feedback from our team, we’re leaning towards buttoning down the hatches, keeping rent increases low, and focusing on maximizing occupancy in our New England markets. We’re seeing significant softening on new placement rents, I’m interested to know if others are seeing similar trends in their own portfolios and what they're planning to do next year. 

Here are some key takeaways and areas I’m curious to hear others’ thoughts on:

• - Two of our projects have maxed out on rental income and are now ready for an exit. We’ve hit the ceiling in terms of what we can push on rent, and it seems like this year might be the right time to sell.
• - One of our projects has fallen so far behind that the only viable option to get back on track is an early exit. It’s a tough decision, but we’re adjusting our strategy to align with market conditions and our timeline.

Having come from a corporate background, I'm used to doing these kinds of planning exercises. We take the T12 roll it forward, we strip out anomalies and one-time expenses and then layer in base assumptions and any known large expenses that are planned for the next 12 months. We then use this to compare actuals to throughout the year and normally do a reforecast at the end of Q1 as thing evolve and change.

I’m curious to hear how others are approaching their 2025 planning. Are you seeing similar challenges with rent growth? How are you planning for softening rents and market fluctuations? What are you doing differently this year based on the current market climate than in prior years?

Looking forward to hearing your thoughts and strategies!

@Matt Wan In my opinion, there is never a bad time to buy the right investment property. While it is true that the time of year can influence market activity, as others have mentioned, there is usually a trade-off depending on the season. In tight inventory markets like Boston, I encourage clients to clearly define their purchasing criteria, start looking, and then be patient.

Some of the best deals I have seen or experienced personally happened during unusual circumstances. For example, properties became available at the onset of COVID, during a snowstorm, a hurricane, a major holiday, or after some other unexpected event. Opportunities often arise when others are not paying attention. The key is to be ready, wait for the right property, and adjust your offer based on the strategy you want to deploy.

The time of year is less important than the property itself. If it is the right investment, focus on how you can negotiate the best terms or tailor your offer to the situation. If you find the property in mid-January but don't want to close with snow on the ground, then submit your offer with a 60 day closing and you'll be purchasing it going into spring. Be flexible and keep an eye out for opportunities, as they often come when you least expect them.

@jonathan Greene Great advice! I’d like to add one more point:

Paying for leads on BiggerPockets can work, but it will only get you so far. To really connect with investors here, you need to contribute consistently to the forums and have some of your deals posted on your profile. Many investors on this platform are working to get over paralysis by analysis and they like to dig in and do their research before reaching out.

I’ll admit, I’ve slacked a bit on BiggerPockets lately, but I have plenty of content on other platforms and websites. That said, the number of times I get on a call with a BP lead and realize they have already thoroughly researched me, including my past deals and content, is incredibly high.

This goes to show that the value you put out there matters. Be active, transparent, and provide helpful insights and leads will naturally find their way to you.

@Jordan Ray This is spot on and something we run into constantly in the New England markets, where prices have climbed significantly over the past five years. Whether it’s a multifamily in Boston, a value-add deal in Worcester, or an investment property in Lowell, the key takeaway is the same: the listing price is not the purchase price.

Here’s an example I use with clients: If I sell a 3-family for $650,000 and list it at $599,900, suddenly, it looks like it sold for $50k over asking—“Wow, it must be a great deal!” But if I list it at $699,900 and it sells for $50k under asking, people think, “Wow, that property must have issues.” In reality, it sold for $650,000 because that’s what it was worth. The list price is just a data point used by the seller or listing agent to drive traffic. 

The challenge newer investors face is that overpriced properties tend to sit on the market for 60+ days and they see them all the time. Underpriced properties get scooped up within the first week—often before the first open house. The solution I give them is to narrow their focus on a specific market, study it, and get to know what a good deal looks like. When one comes up, be ready to act quickly and decisively.

And yes, sometimes that means paying over asking—but don’t get caught up in that comparison. At the end of the day, the numbers have to work for you.