All Forum Posts by: Ben Tutewohl

Hi Vishal,

Have you considered Myrtle Beach? I bought an oceanfront condo there this spring with a partner, and it's on track to cash flow very well, projecting 15%+ cash-on-cash return.

Just to be clear, I’m not a broker and not trying to sell you anything, just another out-of-state investor who was looking for better cash flow and a lower entry point, and so far, it’s been a solid move for us.

We worked with a great realtor, Bradley Klein at The STR Shop, who specializes in short-term rentals in the area. One big advantage is how easy it is to self-manage: the HOA handles all the common areas, and the highest-performing units seem to be luxury studios and 1-bedrooms. They're more affordable to buy and furnish than full houses or cabins, and fewer guests means less wear and tear.

One heads-up: many of the oceanfront buildings are considered condo-hotels, which can make financing tricky. We still got it done, but the loan terms weren’t ideal. That said, even with the tougher financing, the numbers still work well for us.

Happy to share more details if it’d be helpful!

I knew going into it that STRs wouldn’t be passive. But it’s hard to quantify the burden they can place on you. You might only spend a few hours a week actively managing a property, but those hours are completely unpredictable and they almost always pop up at the worst times. A guest can’t figure out the smart lock while you’re at dinner. Your cleaner cancels the morning of a check-in. A toilet backs up at 11 PM. You can’t plan for these things, and they demand your immediate attention.

That constant, always-on pressure can be mentally draining. It’s not just the time, it’s the availability that wears on you.

I’ve been able to handle a handful of STRs so far because I’m young and in a hustle season of life. But this experience has made it clear that I don’t want to do this forever. When the time comes to start a family, I fully plan to repurpose my rentals and offload management contracts so I can be fully present with them.

Self-managing STRs can be rewarding and profitable, but they absolutely come at the cost of your time, your peace of mind, and your flexibility.

Hi Henry, 

Adding an STR property to your portfolio to speed up growth seems like a smart decision based on your situation, especially if/when 100% bonus depreciation comes back.

You're right to think that managing one STR will likely take as much time (if not more) than managing several LTRs. It will probably require significantly more time and effort than your two LTRs combined. Luckily, the increase in revenue from STRs compared to LTRs is often significant enough to justify the extra time and effort. And there are ways to limit your involvement while remaining more profitable than LTR investing.

1. Self-Managing: There are many automations now that make self-managing with a full-time job very doable. If you are able to set aside some time upfront to learn how to self-manage effectively this is defiantly an option to consider and probably the right starting point. If you end up hating it, you can always hire a PM or Co-Host. 

2. Hire a Co-host: Most Co-Hosts will take care of guest messaging, create an attractive listing, and schedule cleaners and other contractors on your behalf. If you go this route you will still have some involvement but it will be drastically reduced. 

3. Hire a full service property manager: If you go this route it will become very passive, hypothetically less involvement for your than with your self-managed LTRs. STR PM's often get a bad rep because they won't care for your property as much as you and they charge high fees which may be true in a lot of cases, BUT, going this route still will likely put more money in your pocket than an LTR and be as passive so its worth considering.

I'm not an expert on the Grand Lake area, so I won't comment on your projections, but I do think looking at turnkey, furnished properties is a smart move for a first-time STR investor. Furnishing and designing a property, especially from a distance, can be more work than you'd expect.

One of the most important lessons I’ve learned is to set clear, realistic, expectations and to exceed them.

If your A/C struggles when temps hit 90+, or you have a cabin with weak cell service, put that front and center in the listing. It might feel risky to call out imperfections, but it builds trust and helps guests self-select. Most people are totally fine with quirks as long as they know about them ahead of time.

Surprises lead to disappointment, and disappointment leads to bad reviews. Honesty leads to happy guests.

Hey Jack,

As someone who was in very similar shoes a few years ago, I’d advise against borrowing money against your parents’ house. You've clearly put a lot of thought into your plan and taken the time to educate yourself, which is awesome.

But the reason I wouldn't borrow against there house is that you’re going to succeed regardless. You’re stepping into a lucrative field at a very young age, and you’ve got the hustle, the smarts, and a strong support system behind you.

So why risk your most important relationships just to get there a little faster? And why go in so big with no experience? The strategy I followed, and would recommend to you, is to lean on your parents in smaller ways, like helping with living expenses while you get started. It’s also huge knowing that if things go south, you've got a place to stay while you get back on your feet.

I would recommend starting by growing your portfolio slowly and sustainably and focusing on learning. House hack, manage rentals, wholesale, flip houses, partner with friends, work for free under a mentor, whatever you choose just focus on learning and working on as many deals as possible.

It might not be as flashy as going all-in and buying a bunch of rentals right away, but those first few deals are usually more about learning and gaining experience than making real money and you want that learning curve to be on your own dime, not your parents’.

Wishing you the best of luck! Happy to chat more or connect if it’d be helpful.

Hey Jon, smart move holding the flip as an STR!

As @John Underwood and others said, if you can manage a flip out of state, you can definitely manage an STR. I'm in year two of doing it and one often-overlooked piece is having a third party occasionally check in. Even great cleaners won't always mention things like overflowing trash, weeds, or backyard mess.

I learned that the hard way, our trash bin kept overflowing, and I didn’t know until a guest left a bad review. Now I have my realtor that sold me the house do a quick monthly walk-through (less than 5 minutes) to flag anything I’d miss from afar. Same way you would have someone check in on a flip so you're not relying 100% on your GC’s updates.

Whether it’s your GC, realtor, or a friend, having someone local check in now and then makes a big difference. Happy to chat more if helpful, good luck with the launch!