Just Starting out

[Adam Zdrojewski]

Hey everyone — new here and looking for some honest guidance before I make any moves.

Quick background: I'm based in western New York and have $200k+ available to invest. My interest is in short term rentals, specifically in vacation destination markets — ideally places I could eventually see myself spending time or even living in someday. So this isn't purely a numbers play for me, there's a lifestyle component to it as well.

The bigger picture goal is to use STR income to first supplement my full time job, and eventually replace it altogether. I'm not naive about what that takes — I understand it's a lot of work, especially in the early stages, and I'm genuinely okay with that. I'd rather put in the effort here vs a 9-5 corporate gig. I'm curious if that level of income is achievable as a lot of my Instagram algorithm is all ads that sound too good ot be true. When something seems to good to be true i become VERY skeptical.

Here's my honest situation: I have the capital, I have the motivation, but I also have a healthy dose of skepticism. A lot of the content I've come across feels like it's produced by people selling courses, tools, or management services — which makes it hard to get an unbiased read on what actually works right now. I know the STR market has softened in a lot of places since the COVID boom, and I don't want to walk into this blind.

I recently came across The Short Term Shop and found their approach interesting — I'm actually signed up to attend one of their open office hours calls to learn more. But before I do, I'd love to hear from people who have been through this — both the wins and the losses. I'm not looking for hype, I'm looking for reality.

Some specific things I'd love input on:

- For someone starting out with $200k+, what markets are actually worth looking at right now for vacation STRs?

- What do you wish you had known before your first purchase?

- Is The Short Term Shop worth engaging with, or are there better paths?

- What does a realistic first-year look like — cash flow, occupancy, headaches?

- For those who have scaled to replace a full-time income, how long did it realistically take and how many doors did it require?

- Any markets you'd specifically avoid right now, and why?

Appreciate any candid feedback — the good, the bad, and the ugly. Thanks in advance.

[Collin Hays]

- For someone starting out with $200k+, what markets are actually worth looking at right now for vacation STRs?

That's going to depend on what your idea of "worth it" is. What is your goal?  

- What do you wish you had known before your first purchase?

If the question is about surprises, I don't know that I had any particular surprises. I guess my biggest surprise is that folks are easier on my properties than I thought they would be.

- Is The Short Term Shop worth engaging with, or are there better paths?

For investing, I don't know that "engaging" with any third party is a particularly good idea. Most of the time, a third party's goals and objectives are not aligned with yours. Have you ever met a realtor that said now is not a good time to buy or sell?   

- What does a realistic first-year look like — cash flow, occupancy, headaches?

The answer depends on a hundred different variables.  Debt, location, your definition of a headache, etc.

- For those who have scaled to replace a full-time income, how long did it realistically take and how many doors did it require?

That's going to depend on your income and what kinds of deals you make. I've been investing in short term rentals since 2005, and I've never replaced my primary income with it. But that would be a tall hill to climb. I would suspect you are going need to be in the hotel business to realistically do that.

- Any markets you'd specifically avoid right now, and why?

Most places in the U.S. can support at least some level of short-term rentals. It's about the deal you get.  Orlando may be saturated, but if I buy out of foreclosure for fifty cents on the dollar, a newer home with a pool near Walt Disney World, I'm going to come out ok.  Avoid any area that prohibits short-term rentals, and avoid neighborhoods that for some reason do - your neighbors will hate you for opening a hotel next door and make your life miserable.