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Alison Pidgeon
  • Lancaster, PA
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First time STR Investor in Pittsburgh, PA -- Need advice!

Alison Pidgeon
  • Lancaster, PA
Posted Nov 26 2022, 15:38

Hello! I read through some posts, but didn't find anything recent related to what's happening in the Pittsburgh, PA market in terms of short term rentals and investing. I am looking to buy a property for a short term rental, but also to use when I travel to the area for work. My office is in Oakland, but I am open to renting anywhere "the numbers work." I am looking at: Shadyside, Squirrel Hill, Downtown, Southside, Mt. Washington, the Strip District and Oakland. Are these good areas for STR? Are there any areas you would recommend I look at that I did not list? I am familiar with commercial investing so this would be my first residential/STR investment and I want to make sure I am choosing the right location and/or potentially filling a niche that is not common in that area. Any other advice you have about the Pittsburgh market would be helpful!

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John Underwood
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#1 Short-Term & Vacation Rental Discussions Contributor
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John Underwood
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Replied Nov 26 2022, 16:17
Quote from @Alison Pidgeon:

Hello! I read through some posts, but didn't find anything recent related to what's happening in the Pittsburgh, PA market in terms of short term rentals and investing. I am looking to buy a property for a short term rental, but also to use when I travel to the area for work. My office is in Oakland, but I am open to renting anywhere "the numbers work." I am looking at: Shadyside, Squirrel Hill, Downtown, Southside, Mt. Washington, the Strip District and Oakland. Are these good areas for STR? Are there any areas you would recommend I look at that I did not list? I am familiar with commercial investing so this would be my first residential/STR investment and I want to make sure I am choosing the right location and/or potentially filling a niche that is not common in that area. Any other advice you have about the Pittsburgh market would be helpful!


 Look on Vrbo and Airbnb for these areas and see what sucess is being had there.

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Michael Baum
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  • Olympia, WA
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Michael Baum
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  • Olympia, WA
Replied Nov 26 2022, 23:18

Hey @Alison Pidgeon, @John Underwood said it best. Take a look at the areas you listed on both VRBO and AirBNB to see what is available and what they are going for.

First, check and see if it is legal to do STRs in the areas you listed first. They whittle it down.

Are you looking for something as a vacation rental or more traveling folks? I am not familiar with the areas but what would bring folks to those areas?

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Alison Pidgeon
  • Lancaster, PA
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Alison Pidgeon
  • Lancaster, PA
Replied Nov 27 2022, 02:52

@Michael Baum @John Underwood Thank you for the reply. I have done research and it seems those are all popular places to have short term rentals. I was hoping to hear from someone local who has a short term rental in the area to fill me in on what I can't learn from doing internet research.  :  )

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Tyler Winget
  • Real Estate Consultant
  • Indianapolis IN + Poconos, PA
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Tyler Winget
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  • Indianapolis IN + Poconos, PA
Replied Nov 27 2022, 06:10

Hi @Alison Pidgeon! PA realtor and Pittsburgh STR host with rentals in downtown next to the PPG, North sector, Mexican War Streets, Allegheny, stretching to Lawrenceville.

All good locations, as are those that you had mentioned.  

If I can answer any location-specific questions, feel free to shoot me a message  off the Thread.

Happy to help!

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Tyler Winget
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  • Indianapolis IN + Poconos, PA
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Tyler Winget
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  • Indianapolis IN + Poconos, PA
Replied Nov 27 2022, 06:16

didn’t want to forget my contribution…

Squirrel Hill is growing in popularity, fast. Big Tech giants are planting out there next to Google. 

Mt Washington, my absolute favorite neighborhood simply because of the VIEWS up there are so underrated (see pics). I was looking for an investment up here a few months back, but they don’t come easy.

Hope this helps!

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Gerald Pitts
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Gerald Pitts
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Replied Nov 27 2022, 06:25
Quote from @Alison Pidgeon:

@Michael Baum @John Underwood Thank you for the reply. I have done research and it seems those are all popular places to have short term rentals. I was hoping to hear from someone local who has a short term rental in the area to fill me in on what I can't learn from doing internet research.  :  )

Vacation rental markets are good. Think mountain, lakes, beaches, skiing. Check out STR insights. It mentioned a few Pennsylvania markets for good ROI last time i looked. Join some local investor meetups as well.


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Alison Pidgeon
  • Lancaster, PA
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Alison Pidgeon
  • Lancaster, PA
Replied Nov 27 2022, 06:37

Thank you @Tyler Winget that is very helpful! Do you have a property management company for your STR's or do you do it yourself?

What is your expected monthly profit on average? How many nights a month are your properties rented on average? Thanks!

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Patrick O'Shea
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Patrick O'Shea
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Replied Nov 27 2022, 08:31

Alison, I have a 6 unit building in Southside and I rent two of them right now as mid-term rentals to traveling nurses on Airbnb. They are booked out 6 months solid with all the healthcare facilities in the area. I'm earning twice the LTR rate and I plan to move other units to this model as leases expire. I know your talking about STR, but this model avoids the tax on rentals less than 30 days and I find management pretty easy with less turnover. I've been doing this for 6 months.

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William Beck
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William Beck
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  • Branson, MO
Replied Nov 28 2022, 08:51

Not sure if this helps but I worked with a few people in Seven Springs about an hour southeast and they were pretty successful. I always get a little concerned about urban STR's just in general due to constant ebbs and flows in the regulatory environment... and NIMBY's. Also, Logan, OH is a top place that flies under the radar but that might be far.

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Alison Pidgeon
  • Lancaster, PA
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Alison Pidgeon
  • Lancaster, PA
Replied Nov 29 2022, 08:55

@Tyler Winget just sent you a PM! And thanks for the insider info!

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Alison Pidgeon
  • Lancaster, PA
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Alison Pidgeon
  • Lancaster, PA
Replied Nov 29 2022, 08:56

@Patrick O'Shea that's a great tip! If I didn't have to stay there on a somewhat regular basis, I would definitely do that. Do you advertise to the health care systems? Are they who pays the rent or does the individual pay? I am curious how this works! 

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Patrick O'Shea
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Patrick O'Shea
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Replied Nov 29 2022, 09:55

I have used Airbnb and FurnishedFinder. About 30% of Airbnb's business is stays of 30+ days. Furnished Finder caters to furnished, 30+ day stays. You can get an idea for area pricing and popularity from both of those websites. I haven't reached out to hospitals, but I would suppose it couldn't hurt. I understand much of those booking are only a week or two out from when they need them, but I'm booked out 6 months. If I find I need to improve my guest pipeline, I'll look into that idea, thanks!

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Patrick O'Shea
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Patrick O'Shea
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Replied Nov 29 2022, 09:58

It sounds like all the surrounding areas suggested in this thread are solid. I would avoid downtown. Although there have been some retail improvements there, there are plenty of undesirables in the area.

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Qiu Jennifer
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Qiu Jennifer
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Replied Dec 2 2022, 18:53
Quote from @Patrick O'Shea:

Alison, I have a 6 unit building in Southside and I rent two of them right now as mid-term rentals to traveling nurses on Airbnb. They are booked out 6 months solid with all the healthcare facilities in the area. I'm earning twice the LTR rate and I plan to move other units to this model as leases expire. I know your talking about STR, but this model avoids the tax on rentals less than 30 days and I find management pretty easy with less turnover. I've been doing this for 6 months.

@Patrick O'Shea, This is really encouraging! I've been looking into mid-term rental investment opportunities for traveling nurses. However, as a new MTR investor outside of the healthcare system, I have very limited knowledge about the actual demand of traveling nurses at the different hospitals. Would you mind sharing which healthcare facilities / medical complexes investors should consider staying close to for mid-term rental? Much appreciate it!

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Patrick O'Shea
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Patrick O'Shea
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Replied Dec 2 2022, 19:13

Qiu, what part of town are you in Pittsburgh? My units are in Southside and there are a number of UPMC hospitals within 15 minutes. Additionally, there is Allegheny Hospital System and others to the east. It's kinda a leap of faith, but knowing the hospitals in the area it was calculated. I've heard a decent way to judge mid-term rental demand is to see where the extended-stay hotels are located. They have already done the research and made the investment in that particular area. I hope that helps...

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Qiu Jennifer
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Qiu Jennifer
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Replied Dec 3 2022, 12:05
Quote from @Patrick O'Shea:

Qiu, what part of town are you in Pittsburgh? My units are in Southside and there are a number of UPMC hospitals within 15 minutes. Additionally, there is Allegheny Hospital System and others to the east. It's kinda a leap of faith, but knowing the hospitals in the area it was calculated. I've heard a decent way to judge mid-term rental demand is to see where the extended-stay hotels are located. They have already done the research and made the investment in that particular area. I hope that helps...

This is really helpful! Thank you so much for the insights!

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Account Closed
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Replied Dec 6 2022, 06:43

I had a condo a few years ago in Hidden Valley ski resort about an hour from Pittsburgh. I personally prefer Hidden Valley over Seven Springs because it was much more of a family place. Our condo overlooked a forest reserve and we could see the orange glow of Seven Springs on the far side of the forest. Winters were booked solid. Place was absolutely beautiful in the summer. A pool/rec center (the one on top of the mountain) was a short walk.  The resort is located reasonably close to Falling Water, kayaking/tubing, bike riding, camping… We were surprised that the summers were booked as well. I might be wrong, but I think Hidden Valley and Seven Springs were purchased by Vail.