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All Forum Posts by: Shaylynn O'Leary

Shaylynn O'Leary has started 5 posts and replied 21 times.

Post: Fix & Flip or Buy& Hold??

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 21
  • Votes 34
Quote from @Matthew Crivelli:
Quote from @Shaylynn O'Leary:

I am currently looking at my first investment property. The property needs to be rehabbed. Initially we thought we would flip, but now we're thinking of holding and using the equity for future investments. What formula or criteria do you use to decide whether to flip or to hold? I'm interested in hearing different perspectives. Thank you.

@shay The biggest question  - can the property cashflow after paying for the costs of holding the property? If you cant turn a decent profit on a monthly basis, it's not a great long term play and you should sell the property.


@Shaylynn O'Learyundefined


 Hi Matthew! Yes, the property will cashflow! We are leaning towards holding it and doing a refi to deploy capital on future projects. My long term goal is to have the "smally but mighty" portfolio and pay off properties as quickly as possible. I have a W2, so the extra rental income would be reinvetsed into the property. Thanks for your response!

Post: Fix & Flip or Buy& Hold??

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 21
  • Votes 34

I am currently looking at my first investment property. The property needs to be rehabbed. Initially we thought we would flip, but now we're thinking of holding and using the equity for future investments. What formula or criteria do you use to decide whether to flip or to hold? I'm interested in hearing different perspectives. Thank you.

Post: Your advice on MTR’s in Montgomery

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 21
  • Votes 34
Quote from @Jeremy Jareckyj:
Quote from @Shaylynn O'Leary:

Hello all, 

I’m thinking of putting an offer on a place in Montgomery. My plan is MTR. What do you know about MTR’s in the Montgomery market? Any advice is very much appreciated. 


 My friend has two MTRs here and he does really well! has been for years .. 

I would try to find a short term/mid term rental friendly agent who might be able to give you super accurate feedback on the market

@Jeremy Jareckyj Thank you for your insight. Is your friend that has the MTR's in Montgomery on Bigger Pockets?

Post: New Investor: Cleveland vs. Columbus

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 21
  • Votes 34
Quote from @Jessica Larson:

Hi Shaylynn, how exciting to be starting your real estate investment journey! You are definitely on a good path right now by looking into the Ohio cities. As some others mentioned, it can come down to if you are looking for cash flow or appreciation. Cleveland is known for cashflow, and Columbus is known for appreciation. It is also VERY important as an OOS to have a good team with boots on the ground to help you on your journey. They know the ins and outs of the city and will be able to assist you to find the right deal for you. If you have a good team in place to walk you through the process, you will be golden. Luckily, if you invest in Cleveland, I know a really great team who has a top sales team and a professional property management company in-house. I would be happy to connect and share more. Wishing you the best!


 Thank you!

Post: New Investor: Cleveland vs. Columbus

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 21
  • Votes 34
Quote from @Yiwei Cheng:

Hi Shaylynn!  Both are great options!  Why not look for properties in both locations and see which numbers work better?  Lots of deals are property specific, like each property make different $$.  You don't have to limit yourself from the beginning.  Evaluate each deal/property on its own.  There are opportunities in every market.


 Excellent point. Thank you. 

Post: New Investor: Cleveland vs. Columbus

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 21
  • Votes 34
Quote from @Scott Allen:

@Shaylynn O'Leary

Columbus is a mixture of cashflow and appreciation (more diverse businesses and growing population). Some neighborhoods will cashflow better than others. Great for house-hacking, multi-family investing, long-term holds, and BRRRR's if you're local and able to manage contractors.

Cleveland is a heavy cashflow market but low appreciation. Some investors look strictly for cashflow but do not care about other things like if a growing population or drivers in the market.

Build a core four in both markets and hunt from there. Get you feet your wet and just have a learning mindset on your first one. 


 Thank you! I'm leaning towards Cleveland for the cashflow. I would like to get out of my W2 in the next three years. 

Post: New Investor: Cleveland vs. Columbus

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 21
  • Votes 34
Quote from @Samuel Diouf:

I would start with Columbus. You will see great returns when leveraging your money due to appreciation and you will have less risk involved as the Columbus market as a whole is growing at a rapid pace. 


 Thank you! Do you feel the competition is higher in Columbus than Cleveland?

Post: Your advice on MTR’s in Montgomery

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 21
  • Votes 34

Hi Zachary,

Thank you for your response! Yes, I know how to evaluate metrics for MTR in a given market. I guess I should have worded my post differently. My inquiry is more of hearing someone's first hand experience in Montgomery with their MTR. For example, I've recently spoken to someone about their MTR in Montgomery and they shared their MTR experience has seasonal occupancy, hard to find boots on the ground, contractors are slow and many do not take credit cards for payments, etc. Things that you would only be privy to actually being in the market.

Thanks for you help and input. I sure appreciate it. 

Post: Your advice on MTR’s in Montgomery

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 21
  • Votes 34

Hello all, 

I’m thinking of putting an offer on a place in Montgomery. My plan is MTR. What do you know about MTR’s in the Montgomery market? Any advice is very much appreciated. 

Post: New Investor: Cleveland vs. Columbus

Shaylynn O'LearyPosted
  • New to Real Estate
  • Central Oregon
  • Posts 21
  • Votes 34

Hi Simon, 

Thank you for your response. My ultimate goal is to replace my W2 income. Eventually, years down the road, I would like to sell some of the properties that I have acquired to pay off other properties and own them free and clear. Much like the model in Chad Carson's book, The Small and Mighty Real Estate Investor.