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All Forum Posts by: Ryan O'Leary

Ryan O'Leary has started 13 posts and replied 45 times.

Post: San Antonio Property Management

Ryan O'LearyPosted
  • Texas
  • Posts 45
  • Votes 10

Good afternoon team,

I’m looking to provide my buddy an experienced property manager/management company in the San Antonio, TX area. He’s got one property that he’s house hacking right now being used as a mid-term rental as he’s focused on school. Current company isn’t panning out as expected and I’d like to set him up for success. 

Anyone have any referrals? 

Any information would be greatly appreciated. 

Ryan

Post: Investment Strategy Advice

Ryan O'LearyPosted
  • Texas
  • Posts 45
  • Votes 10
Quote from @Kerry Baird:

Throwing in my .2 as a veteran who also bought houses where we were stationed. You may have more VA entitlement that would allow another use of the VA benefit, or maybe you used it all. We saved our VAs for after the military, and got a number of owner occupied houses that we improved over time, and sold or turned into rentals.

When you say you are debating whether to sell a place to have a paid off house…it currently *is* a vehicle to purchase additional properties. It produces so much cash flow…consider getting another HELOC on your primary while you currently live there (so hard to get one on a rental). Buy a place with the HELOC, rent it. Use the cash flows from all the rentals to pay off the HELOCs quickly. Do that again. And again. How much CF from rent do you have in total? Navy Federal does high limit HELOCs on primary houses, and you would have to get one before you move out into your next owner occupied residence.

You could buy with owner occupied 2 more times, once per year, in the SA area and then in the future school assignment locale.  After those 2 years, you will be posted elsewhere, so buy another owner occupied in year 1 and a second owner occupied in year 2 of your next assignment.  By this time, your rentals will have amassed funds for future down payments.

My original goal was 5 houses, paid for, to replace my pension (I did 6 active, 4 reserve and got out to be Mom).  At the end of the military road, the rental income is around 10 times more than my hubby’s pension.  I bought a total of 39 houses, some we fixed and flipped, most we rented.


Kerry, I'm sorry I missed this. That could be another option in getting a HELOC on the current property. Right now I'm using my primary (4-plex) cash flow and paying down a HELOC (scheduled to be paid off May 2024) and then for future pay downs towards mortgage principal on my hawaii condo. Total cash flow with all 3 properties will be about $3k. Props on purchasing 39 properties in that time span! Definitely looking to do that one day.

Post: Investment Strategy Advice

Ryan O'LearyPosted
  • Texas
  • Posts 45
  • Votes 10
Quote from @Colleen F.:

@Ryan O'Leary Do you have a 4 plex or are you renting a single family by the room?  Because if it is the later the biggest issue will be management when you are stationed somewhere else. If you can rent it as a single family profitably I would likely do that when I leave the area, if not sell it and move on to another area. The reason being that it is hard to find a PM to manage rent by the room and any state you rent in on your own without a PM you better know the laws. 

Alot of bars fail and they are not passive, nor is an assisted living, and flips aren't really passive either. And you want to do these activities in the highly regulated state of Massachusetts, keep that in mind. Rentals are considered passive and they can be truely passive so if your focus is on passive that is the direction to go. 

Also if you are going to be a nurse anesthetist in MA that is a 200k a year job you can leverage that income alot if you want to buy rentals. Living below your means is one way to get you to your goals.   If properties are cash flowing why accelerate the payoff? I don't mean to be negative but suggesting after brainstorming  focus and see what works. 

Colleen, it is a 4-plex here in TX renting by the room. The model has worked well so far with minimal vacancy. I’d like to keep it going like that, partner with a PM who can mix long-term rent by the room and maybe one unit as an AirBnB arbitrage while I’m in school.

I’d like to use the cash flow and pay down the other rentals so I could build that cash flow/month. The extra money through CRNA will definitely be used for bigger projects… maybe not a bar, but larger commercial apartment complexes. Haven’t done anything over 4 units yet but want to. 

thanks for getting back to me!

ryan

Post: Investment Strategy Advice

Ryan O'LearyPosted
  • Texas
  • Posts 45
  • Votes 10

@Becca F. yes the HELOC has been a pain, but a learning experience nonetheless. If I were to pay off the MA property, it would be worth around $400k. At the time, I would be able to get 70% LTV, so it was somewhere near $300k line of credit.

I'm leaning more towards cash-out hen the time comes. Definitely check that episode though!

Post: Investment Strategy Advice

Ryan O'LearyPosted
  • Texas
  • Posts 45
  • Votes 10

Good afternoon BP family. Wanted to share my current situation and gather some advice. 

BLUF: Do I sell my current property to pay off another so that I can take a massive HELOC out to BRRRR a multi-family home every year until I retire from the military (12 more years)?

Background: Currently, I live in a 4-plex in San Antonio that we rent by the room for the other 3 units, cash flowing $2400/mo. I have about $200-250k of equity in the property. Need to live here for a minimum of 2 more years due to starting grad school in May 2024, carrying me through May 2025 where I'll have to move somewhere else for two years finishing the program (military anesthesia program). Rate is 2.85% through FHA loan.

I have a SFH in Massachusetts that I want to pay off (and keep in the family). Pay off would be $145-150k and I have an existing $80k HELOC against this house that I'm consistently paying down ($25k to go).

My last property is a 3/3 Condo in Hawaii that has been consistently rented since I first house-hacked it back in 2018. I refinanced to 2.25% back in 2020 and plan to keep it for a few more military PCS cycles, allowing further appreciation. Con... my VA loan is tied up in this house.

I put a lot of work into this San Antonio 4-plex and the rent by the room situation has been phenomenal. Debating whether to sell it to have a house paid off that I can then use as a vehicle to purchase additional properties to build the portfolio. 

Mass SFH estimated value: $395k. Estimated new HELOC would be about $300k.

Goal: After hearing Episode 395 with Thach Nguyen, him pulling in $100k/month passively was eye opening and something I wanted to do for my family. If everything goes right, with an officer pension and a CRNA W2 job when I leave, plus working to pay off multiple rentals, I feel like the $100k/month is attainable. 

Career/life goals: 

- $100k/month passively

- Would like to one day open an Assisted Living facility back in MA using real estate tools to potentially fit out larger SFHs, hiring other nurses/aids

- Would like to 2-3 flips/year to pay off some of the rental properties to increase that monthly passive income

- I love nursing as of now, so I don't know if I would drop the license after retirement.. would keep a W2 going but I know it'll hinder scalability

- Played pickle ball for the first time the other day in San Antonio and I want to build a bar/facility back in MA as a hobby

I'm all over the place with the goals, but any advice on whether to maintain the buy and hold strategy vs selling one off to pay one off would be greatly appreciated. Thank you team!

- Ryan 

Post: Should I hold or sell and reinvest?

Ryan O'LearyPosted
  • Texas
  • Posts 45
  • Votes 10

@Nick Bauer

Hey man, if you haven't used your VA loan yet, you could snag a SFH in Hawaii and house hack it. I've been doing it the last 2.5 years and through a deployment. I will probably rent it for one or two more PCS cycles before I sell it. Rates are crazy low for the VA. Just watch out for pricey HOA fees out here... it's the only thing holding me back from keeping this property in order to break even with rental income. I'll have made about $60k extra rental income on top of what we already get via BAH.

Stay safe brotha.

- Ryan

Hello BP, 

I have friends and family that are investing with me in my next real estate deal. This would be my first syndication-type deal, and I want to make sure I'm doing everything right. I'd like to have everyone's investment secured by the property that we'd be purchasing. I'm thinking about putting all of us into an LLC, but are there any other options? Does anyone have a recommendation for a real estate attorney in San Antonio?

Thanks everyone!

- Ryan 

@Jaysen Medhurst thanks for the feedback man. Ya I’ll definitely have to look into the gift of equity for tax purposes. I won’t be keeping it long term, but we’ll see how it plays out. Nothing closed or locked in yet.


- Ryan

Hello everyone, I had a question on financing for a SFH:

I will be purchasing a SFH from my parents for 160k. The house is worth 240k from our last appraisal in February when my parents had bought out the beneficiaries of my grandparent's house, and left their 80k into the house as equity.


It is currently rented to the same renters over the last 12 years. We raised the rent to $1500 that starts August 1st of this year and on a 12 month lease. My parents got a 30-year loan with very little money down, but all local banks that I have been calling are offering ARM deals. I have yet to do an ARM for financing, but I'm wondering if I should be looking at a 7/1 ARM financing or 30 year loans?

The plan is to immediately take the equity and get a HELOC on the property in order to do rehabs on some other properties, if that's possible.

I'll continue calling local banks to see what they offer but I wanted to shoot a description of the deal here in case anyone had their alerts set up!

Any info is greatly appreciated. Thanks! 
 

Post: Worcester MA Investing

Ryan O'LearyPosted
  • Texas
  • Posts 45
  • Votes 10

@Joshua Bernhardt hey man, nice to meet you. Ya worcester is blowing up from what I can see, hear, and read through forums and other news outlets. Boston firms are coming in and buying some high rises to turn into apartment complexes. Multiple new restaurants and breweries coming in. It’s great to see. 

Personally, I haven’t invested (yet) into worcester because I’m in line to buy a property within the surrounding towns of worcester. I would love my future rentals to be within worcester to make it easier to manage myself before hiring out a PM company, but being military, I may invest in other parts of the country. 

For worcester, the stadium is being built around Madison Street. Kelley Square, a notoriously horrible intersection, is currently getting rebuilt, with multiple restaurants going near it as well. Your main roads are Rt 290 (all over worcester), Rt 20 (Auburn, Millbury both great towns) and Rt 146 (leads to border of Rhode Island).

Hope this helps man!