All Forum Posts by: Ryan O'Hara

Quote from @Will Fraser:

Atta boy @Ryan O'Hara!  Way to play the best game as a family!

 Completely agreed! Took a while to get my wife on board, but it's worked out well so far!

Quote from @Katie Miller:

@Ryan O'Hara Ryan! This looks like a really cool property and I'm super curious about how you work with the long-term tenant above a airbnb. Does the LT tenant care or ever had issues with the ST guests downstairs? Do they meet them or see them at all? 

 Hi Katie - Our tenant is very easy going and is very outgoing. She thoroughly enjoys when she gets the opportunity to meet them. The only issues that we have run into is that the house is old and is hardwood floors throughout so guests hear her walk around from time to time.

Quote from @Patrick Drury:

@Ryan O'Hara
Property management. You can own hundreds of units but the question is can you manage them efficiently? If you are local you should learn how to manage your properties unless your day job is too demanding then keep the day job and have someone else manage them till you are at the point of quitting the day job and managing them. Property management is a really good skill and crucial role. 

Hi Patrick, I appreciate the recommendation. I do plan on managing my first few properties myself, but hope to eventually get to the point to have a full time property manager as I continue to grow. I am, more or less, looking for other roles out there to gain experience within the industry.

Bruce - I appreciate the response. The strategy is a very gray/flexible strategy so if something does come up that allows for a bigger purchase or the opposite with wait a year between purchases, it can bend to that. I know it isn't a perfect strategy, but I wanted to have something on paper so that I can have some sort of long term goal even though it may change 1,000 times over that time. 

I am still learning the financing side of things which is why I want to find a career within the industry so that I can learn by doing. 

Hi Patrick, I appreciate the recommendation. I do plan on managing my first few properties myself, but hope to eventually get to the point to have a full time property manager as I continue to grow. I am, more or less, looking for other roles out there to gain experience within the industry. 

Over the last few weeks, I have been working on my long term goals (14-15 years) within real estate and life as a whole. Essentially, I want to systematically grow my portfolio over the next 14 years by adding a door to the formula each year (example: Bought 3 in 2022. Goal is to buy 4 in 2023, 5 in 2024). After breaking that down and really pinning down what I want to do long term in my career, I am looking to dive head first into the real estate world. 

Currently, I am in software sales, but I want to see what roles are out there in the real estate world. I am a big believer in doing the work to learn rather than only  learning in the classroom (i.e. reading books/listening to the podcast). While I know there are the obvious roles like agents and property managers, I wanted to see if there are other roles to learn the industry as a full time career rather than side hustle for the time being. What roles are out there to show the ins and outs of the industry?

Investment Info:

Small multi-family (2-4 units) buy & hold investment.

Purchase price: $337,000
Cash invested: $50,000

My wife and I are house hacking a 3-unit property with a long term tenant and Airbnb in the basement allowing for cashflow.

What made you interested in investing in this type of deal?

This was our first deal, and was the best way for us to get into a house and start our journey.

I am currently house hacking a 3 unit property with a long term tenant and STR. I have been breaking down my long term plans within real estate, and want to put the pedal to the metal going into 2023. I was wondering if there is anyone in the Milwaukee area who would be open to connecting in the coming months to discuss the Milwaukee market and talk a bit of shop around how to navigate the area/growing the portfolio.

Thank you in advance! 

-Ryan

My wife and I recently purchased our first property that we plan on house hacking. We are inheriting a tenant and plan to have an STR in the basement unit.

Now that we are officially in the game, I have been wondering how do we go from 1 property to 2,3,4,5,etc...? The first property was a feat in itself with the money side of things, and convincing my wife that this is the smart route to go. In my perfect world, we would be getting our second property as soon as it makes sense with us moving into the new place.

That said, what are ways that other investors have taken that next step in growing their portfolio? I know there are many routes, but would love to hear from others on what they found to work.

Hello! My wife and I are currently in the process of closing on our first duplex in Milwaukee, WI. We are planning on house hacking, and the lower unit currently has a tenant who has been in the place for the last 25 years. Her current rent is $975 MTM for a 3 bedroom 1 bath place. She has taken incredible care for the place considering how long she has been there. However, the market rent is right around $1,500 for the place with the location and size of the unit. We have been trying to figure out the plan to make the numbers work while not making her want to leave. Our current idea is meeting in the middle at $1250-1,300. That said, what is advice do you have for increasing rent while keeping the tenant happy/understanding?