Scaling to 100+ STR Units Without Compromising Quality

Kaye Putnam: Welcome back to Get Paid For Your Pad. I’m really excited to welcome Troy Daily back to the podcast. This is actually my first time interviewing you directly, so I’m especially looking forward to this conversation. Troy is the CEO of Elevated Stays in Traverse City, where he manages around 95 active short-term rental units, and his portfolio has grown significantly over the past few years.

Before we started recording, we were talking about how cold it is right now. I’m in Chicago, but Troy has kids home from school due to a snow day, so if you hear any background noise, that’s why.

Troy Daily: Yeah, it’s a long winter break. Seventeen days with no school, so we’re right in the middle of it.

**Kaye:**That’s actually a great segue, because your portfolio has grown a lot. We’re recording this just a couple days before Christmas, even though the episode will air later. How do you approach big holidays like this as the CEO of a growing company?

**Troy:**Honestly, it’s kind of a blur. Between kids, travel, and everything going on locally, it’s busy but also a really fun time. We focus on welcoming guests for the holidays and making their stay special, even while we’re juggling all the local chaos at the same time.

**Kaye:**Right, with Christmas parties, school concerts, all of it.

**Troy:**Exactly. Christmas concerts, pageants, everything.

**Kaye:**Do you sit your team down and give a big holiday pep talk, or is it more low key?

**Troy:**It’s a bit more low key. The holidays are still busy for us, but not like peak summer. People want to be home during the holidays, so demand shifts a bit. That said, we still have strong occupancy through the end of the year, and we really try to make those stays special.

For some of our owners and properties, we set up Christmas trees, lights, and decorations. We don’t do it everywhere, but for select homes it adds a lot of holiday cheer.

**Kaye:**Have you noticed a difference in occupancy or ADR for those homes?

**Troy:**Yes, absolutely. We advertise those holiday touches, and those properties do see higher occupancy and higher rates. If you’re traveling for the holidays, you want that homey feeling. You want the experience.

**Kaye:**I love that. We’ve talked about your story in previous episodes, so we’ll link those in the show notes. Today, I want to focus on your acquisition and growth strategy, because it’s a little different.

When you first came into Eric and Jasper’s world, you had about 18 units. Now you’re just shy of 100. I believe you also purchased a building. Can you share that backstory?

**Troy:**Yeah. I’ve actually owned the building for a while, but we’re in the middle of a major renovation. It’s a seven-unit building, and four of the units are being completely remodeled right now. Technically, if you count everything, we’re over 100 units, but some are offline due to renovations and seasonal usage.

**Kaye:**Nice. How much of your portfolio do you own versus manage for other owners?

**Troy:**We have 95 active units right now. I personally own 12 units.

**Kaye:**That’s a solid mix. When did you first buy the building?

**Troy:**We bought it in 2019. It’s an older building from the late 1800s. The first couple of years were about understanding the property and planning for renovation. Last winter, we fully renovated the three lower units, including layouts, bathrooms, everything. This winter, we’re renovating the upstairs.

We debated tearing it down and rebuilding, even expanding from seven units to twelve. But there are regulations here that limit short-term rentals with new construction. When we looked at the costs, we decided a renovation made the most sense. Over the last two years, we’ll have invested over $700,000 into the renovation.

**Kaye:**That’s incredible. Do you have a preference between owned units and managed units?

**Troy:**I focus on understanding what guests are looking for and building a diverse portfolio. All of our units are elevated, but we want a mix of sizes and price points. This particular building will operate more like a boutique hotel. It will be a high-quality experience, but with efficiency-style units rather than traditional hotel rooms.

**Kaye:**That’s exciting. What challenges did you uncover during renovation?

**Troy:**Once we opened up the walls, we found an 18-inch difference from one corner of the building to the other. That meant new framing, roof work, leveling floors. It’s a design-build process. Plans change once you see what’s really there. But we’re excited to turn a 150-year-old building into something really special.

**Kaye:**And it’s close to downtown Traverse City, right?

**Troy:**Yes, just a few blocks away. You can easily walk or bike downtown.

**Kaye:**What’s next for Elevated Stays? Where are you looking for growth?

**Troy:**We’re looking at acquiring smaller management companies locally. We’re also exploring boutique hotel opportunities that align more with an Airbnb-style experience. We want unique properties that offer something different.

**Kaye:**People want experiences, not just another condo.

**Troy:**Exactly. Condos are popping up everywhere. There’s a market for them, but when there are hundreds within a few blocks, it gets tough. Experience matters.

**Kaye:**Your growth has been incredible, especially in the last year. How has your role as CEO changed?

**Troy:**It’s all about leadership now. This is a very operational business. Housekeeping is massive. We brought housekeeping in-house, and earlier this year we brought laundry in-house too. That was a huge undertaking. We manage laundry for nearly 300 rooms.

My focus is empowering the team, putting the right people in the right seats, and making sure everyone understands our goals and values. Once that alignment is there, growth becomes possible.

**Kaye:**What are you most proud of?

**Troy:**Where we are now and what’s next. It’s exciting to see what the team wants to do and grow into together.

**Kaye:**How do you approach vision setting?

**Troy:**The off-season is key for us. Summer occupancy is over 90 percent, but winter can drop to 10 or 12 percent. That gives us time to plan, evaluate systems, tech, and operations. The whole team is involved. I naturally want to push forward, but I’ve learned to slow down and make sure quality and systems stay strong.

**Kaye:**What was the best decision you made this year?

**Troy:**Putting the right people in the right seats. Hiring slow and letting go when it’s not aligned is hard emotionally, but it’s necessary. Our team right now is incredible.

**Kaye:**Is there a role you wish you hired sooner?

**Troy:**Splitting housekeeping and operations into separate roles. Housekeeping is a huge part of operations, but there’s so much more beyond cleaning. Making that distinction earlier would have helped.

**Kaye:**What does your operations manager handle day to day?

**Troy:**Inspections, inventory, owner communication, scheduling, payroll, admin, and essentially HR responsibilities. My role as CEO is owner relations and growth.

**Kaye:**You’ve also seen strong revenue growth. Comparable units are up 33 percent, and total revenue is up over 100 percent. What do you attribute that to?

**Troy:**Quality. We invested heavily in linens, laundry, and consistency. We supply all linens for owners. Everything is hotel-grade, white, pressed. We also focused on small touches like better coffee, welcome gifts, and repeat guest incentives. Airbnb is still a major channel for us, and strong reviews drive everything.

**Kaye:**Are there amenities you consistently recommend to owners?

**Troy:**Good coffee makers are a must. Smart TVs, charging by the bed, all of that is standard. For upgrades, hot tubs and indoor saunas have been huge, especially for wellness-focused guests.

**Kaye:**Is there anything you did in 2025 that you won’t do in 2026?

**Troy:**Saying yes to everything. Early on, I accepted units that didn’t align with our brand. Now we’re much more selective. If owners aren’t willing to reinvest in quality, it’s not a fit.

**Kaye:**That brand clarity is huge.

**Troy:**Absolutely. We even had to make that decision with one of our own older properties. It didn’t meet our standards, so we committed to fully renovating it rather than keeping it as-is.

**Kaye:**When evaluating acquisitions, what do you look for?

**Troy:**Uniqueness and opportunity. There’s room to transition legacy hotels into more experience-driven, boutique-style STRs.

**Kaye:**What’s had the biggest impact on your leadership style?

**Troy:**Surrounding myself with the right people. Growth is hard on teams. Stability matters. Rapid growth creates discomfort, but with the right people, it’s manageable.

**Kaye:**What does a typical week look like for you now?

**Troy:**Owner relations and communication. I write a monthly owner newsletter, handle acquisitions, and communicate the vision. Without owners, we don’t have a business.

**Kaye:**How do new owners find you?

**Troy:**Referrals, SEO, Venturi, and my real estate network. Venturi took time, but after about 18 months, it became consistent.

**Kaye:**This was such a great conversation. Any final thoughts on working with Freewyld?

**Troy:**Revenue management is a full-time job. Having a team that understands the market, demand, and pricing removes stress and drives results. I couldn’t do this alone.

**Kaye:**Thank you so much, Troy. And Merry Christmas.

**Troy:**Thank you. Merry Christmas to you as well.