Michigan Short Term Rentals

Most investors focus on price and projections. Experienced operators focus on financing structure. In this episode, Tony and Jordan unpack two lending products that are changing how they and their clients approach vacation rentals and boutique hospitality. https://michiganstrconference.com⁠ Join the  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Michigan Short Term Rentals Facebook group⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

The 2026 Michigan STR Conference is officially live, and this episode explains  why  this year is different. Tony and Jordan unpack what happens when you get in the right room, around the right people, at the right moment. They share how proximity to high-level operators, investors, and thinkers has directly led to deals, partnerships, clarity, and faster execution in their own journey. This episo...

Tony and Jordan unpack a mindset shift that changes everything: you are not the same person you were when you failed last time. They use an Indiana football clip as a punchy example and apply it to business, fitness, and investing. The core idea is simple. Most people make decisions using a “mechanical mind” that treats past outcomes like permanent limits. But your skills, network, confidence, and...

Tony and Jordan break down a counterintuitive idea: the most interesting person in the room usually is not the loudest or the funniest. It’s the one who listens, asks elite questions, and makes other people feel seen. They talk about how to avoid shallow conversation starters, how to build real connection even when you don’t share interests, and why stories beat facts every time. They also hit the...

This is a candid year-in-review episode focused less on wins and more on evolution. Tony and Jordan unpack the moments that forced them to grow: larger projects, higher stakes, constant problems, and the realization that the next level requires different people, systems, and discipline. They talk openly about calm under pressure, thinking bigger, investing in health, and why the right team matters...

Inside this episode, Tony and Jordan unpack their annual strategy retreat and reveal the three levers that are shaping their next five years of growth. They share why hiring earlier creates the breakthrough, how long-term thinking beats short-term perfection, and how stewardship builds the relational capital needed to scale. It’s a candid look at the decisions, discipline, and mindset shifts drivi...

Tony and Jordan break down how their investor journey evolved from doing a first flip with a close friend to bringing new investors into every deals. They talk through what actually attracts capital in real estate deals proof of action, reputation, conferences, and showing your work in public so money starts coming to you instead of you chasing it. Join the  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Michigan...

Tony and Jordan walk through their newest deal under contract a twenty four unit motel in Southwest Michigan that they have been tracking for years. They break down why they kept coming back to this specific property, how they underwrote it using real comps instead of the seller’s weak performance, and why they are convinced the market can support boutique level rates once they add design and amen...

This episode breaks down the real-world shift Airbnb made to an AI-driven review removal system and how hosts can get negative review removed within the new system. Tony shares the exact framework he used to get two unfair reviews removed in under 90 minutes after weeks of failed attempts. Jordan adds insight on why strong systems, clear guest expectations, and consistent communication make these...

Tony and Jordan make a strong case for a bias toward action. They show how tiny first steps lead to deals, skills, and momentum. From analyzing numbers to touring homes to placing offers, each move compounds. They share how one Stevensville buy opened the door to more properties, a management company, and even a conference. The takeaway is simple. Write the next three steps. Do one today. Repeat t...

This episode is a tactics deck for closing when “the numbers don’t pencil.” Fresh from a conference insight that effectively saved  ~$150K  on a deal, Tony and Jordan break down offer architecture (price vs.  terms ), including  0% seller financing , long amortizations with balloons, and master lease/lease-option approaches that let you invest into operations first and finance later. They walk thr...

Tony and Jordan break down what separates Michigan’s top 1% of short-term rentals from the rest. From hot tubs and privacy to 50-photo listings, perfect reviews, and pet-friendly policies, this data-driven episode reveals what elite operators are doing and how you can apply it to your own property. Join the  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Michigan Short Term Rentals Facebook group⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

Is Q4 secretly the best time to buy a short-term rental? Tony and Jordan break down fall deals, stale listings, cost-seg deadlines, and why onboarding during certain seasons can impact your year one revenue. Join the  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Michigan Vacation Rentals Facebook group⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Connect on  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Subscribe on  ⁠⁠⁠⁠⁠⁠⁠⁠...

Vacation rental SEO veteran Roberto Sidoti breaks down how to win direct bookings today. From local SEO and Google Business Profile to LLM-ready content, smart backlinks, and conversion funnels that actually turn traffic into stays. Rentamira Join the  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Michigan Vacation Rentals Facebook group⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Connect on  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

This episode is a mini-masterclass on hospitality marketing. Steph Weber explains how she financed and launched a 12-cabin riverfront development, marketed it mid-construction, and grew direct bookings. Steph talks all things Instagram/FB, influencers, email capture, retargeting, and paid ads. She details naming, mood boards, guest experience design, and the metrics that matter (engagement → list...

Three lessons. That’s what Tony and Jordan pulled from their trip to Boutique Hotel Con in Tennessee, and they’ll change the way you think about building wealth in hospitality. In this recap, they cover why the people you surround yourself with matter more than tactics, how to spot if you’re only “trying” instead of moving mountains, and why grinding through setbacks is the price of entry for big...

In this episode, Tony and Jordan break down the five biggest lessons they learned from Michigan’s 2025 peak season. From vetting properties more carefully to avoiding unreliable service providers, they reveal the costly mistakes that can drag your business down. Why not all markets are truly “saturated,” and why building a strong team is the ultimate growth multiplier. Join the  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

Tony and Jordan open up about reinventing themselves again. From barber to broker, factory floor to founder, they break down the mental barriers (fear, comfort, “golden handcuffs”) that keep entrepreneurs stuck. You’ll hear how masterminds, better circles, and defining your “perfect day” create clarity; why moving from player → coach → owner changes everything; and how to build confidence through...

Is your STR underperforming? Tony and Jordan reveal  the five revenue multipliers that separate winning properties from average ones . You’ll hear how a few small design tweaks flipped a property from zero bookings to fully booked, why investing in amenities like pools and pickleball courts can deliver huge ROI, and why networking, photos, marketing, and dynamic pricing aren’t optional anymore. If...

This episode gets real about development math. They discuss site work, vertical builds, and amenities, so they’re planning multiple paths: operate as a high-end resort  or  pre-entitle as PUD/site condos to give banks a clear  exit  if needed. They discuss financing realities, raising capital, community alignment, and why scarcity (no true resort-focused stays in the area) creates pricing power. J...

What happens when you take a tired five-unit building and flip it into a powerhouse STR property? Tony and Jordan share the full story of their Southwest Michigan five-unit acquisition from botched arbitrage beginnings to closing on the property with  creative financing and no money out of pocket . They reveal the wins and the challenges. Along the way, they share practical lessons on cutting cost...

In this episode, Tony and Jordan break down Airbnb’s Q2 earnings call and unpack the key insights for short-term rental owners and investors. From revenue surprises to subtle warnings hidden in the details, we explore what Wall Street’s numbers actually mean for Main Street hosts. If you want to understand where the market is heading and how it could impact your business, this episode delivers the...

In this episode, Tony Stancato and Jordan Painter share how they’ve narrowed their motel acquisition focus to one powerful corridor: St. Joseph to New Buffalo, Michigan. They reveal why chasing every “good deal” nearly slowed their growth, the hidden costs of operating outside your core market, and the systems they’ve built to dominate locally. If you’ve ever struggled to turn down opportunities,...

Tony and Jordan unpack one of the biggest mindset shifts for STR operators: chasing consistency instead of perfection. Whether it's installing a new AC  before  it fails in peak season or responding to guests in 10 minutes instead of 40, they explain how consistent execution builds trust, saves money, and reduces stress. They also highlight the importance of culture, team training, and proactive c...

In this episode, we sit down with Dustin Baker from Hidden Gem Media to talk about what most STR owners get wrong about their photos and videos. Better storytelling leads to more bookings. Dustin shares how he blends cinematic visuals with direct response marketing frameworks (like hook, story, and offer) to help vacation rental listings stand out in a crowded marketplace. If you want guests to fa...