Sell then buy or Buy then sell - which is best?

Question

Hello all,

My husband and I are going to put our little duplex on market in June 2026. We have looking to purchase another duplex to house hack as well and get out Eugene city laws that are not in favor of the landlord. Since starting our search we have only found 1 duplex that we wanted to move into in February 2025, but our realtor did not want to put in the offer while we were on vacation and it went pending.
I am not sure which is best, to sell our current duplex, rent, and then buy another one? Or Buy a new one then sell our current duplex? Has anyone been in this situation and what is your experience? What worked for you and what did not?

Samantha Chacon-Johnson · Answer

@Nicholas L.

Yes you are missing a lot. We are selling regardless. We don't not want to be landlords in Eugene anymore or own a house in Eugene.

We want to sell to use SOME of the equity to pay off my student loans. The rest will go into a high yield savings account until we are ready to purchase again. This will buy our financial freedom and allow us to scale faster. More importantly and on multiple different fronts that just fiancés, this will allow us to start a family.

I am not nervous about having multiple mortgage payments if I intend to rent them. I am nervous about having multiple mortgage payments during the sell of our current place and purchase of another one AND not being able to afford it both the mortgages.

Yes one side is rented. Renting the sides we live in will not cover the mortage. I have mitigated the risk by doing more than you described because I self manage. But that does not mean I want to stay in Eugene. Eugene, continues to have more less favorable laws...

Yes, sell, get out of Eugene and purchase a bigger one, Pay of student loans/be done with debt,  start a family, put the rest in a high yield savings account, and purchase another duplex (meaning we would have 2) sooner than if we did not pay off my student loans. Something you may not know about student loans is they accrue interest on a daily basis so in order to get ahead you have to make double the payment and multiple payments a month to disrupt the equation, which you can find at studentaid.gov. Also, our rate on our house now vs house to be purchased would likely be the same. It's a wash.

Real estate is personal. That's why got into it. I knew it was gonna help me with me personal goals and financial goals faster than renting and working my W2. So we went with real estate, build the sweat equity, while working our W2.

Do you have any other advice on our future sell and purchase?

Joseph Tadres · Answer

Hey Samantha! I would keep it if I had enough cash. You have to make sure you find some really good tenants since the city laws are not in favor of the landlord.

Theresa Harris · Answer

As you don't need to sell your current home to buy the next property and you've been actively looking for 8 months and only found one that could work, I'd suggest waiting until you find the right home and buy it.  You can then sell your current home.  Otherwise you are going to have to find a place to live between selling your current home and buying your next home and I know you say you don't mind moving twice, but reality can be different.

Nicholas L. · Answer

@Samantha Chacon-Johnson

hi. this type of question mixes the investing with the personal, so it's tough to answer.  so i'll just give you some things to think about.

-you said you want to use the proceeds to pay off your student loans.  i totally get that.  but, what's the interest rate on your loans?  once you sell... that's it.  all the equity you built up is gone forever.  this is 100% your decision - i'd never tell someone how to use their own money.  but, just pointing this out so you can think through it.

-you're nervous about having multiple mortgage payments.  i totally get that as well.  it IS a big deal!  but, for most of us, that's what investing is - the rent pays the mortgage.  my first rental was a former primary residence that i self managed and after i moved out and rented it, it was rented continuously for 7 years without a day of vacancy.

-if you're house hacking now, isn't one side rented?  keeping it would just mean... renting out the other side, right?  or am i missing something?  yes, OR is a place that favors renters, but the flip side is high demand for rentals.  risks can be mitigated through strict screening, good management, and patience. a high quality property manager can help with all this.

-you want to sell a duplex... and buy another duplex?  wouldn't that one be a rental too?  and wouldn't your rate be higher than whatever you have now?  or is your plan just to house hack and sell again?  that's giving away hard earned equity.

let me know if i am missing something - again, just trying to help you step back and think through this.

Eric Gerakos · Answer

I like to Sell then Sell then Buy. During leap years I do the opposite....

Scott Allen · Answer

@Samantha Chacon-Johnson go in contract on a duplex that you like with a home sale contingency of your current residence. You could use more earnest money to make the offer more competitive if sellers do not like that contingency

Scott Allen · Answer

They're usually about a 45-60 day timeline - it would mainly depend on the timeline of a buyer putting an offer in on your current residence soon after going in contract on the one you find.

Samantha Chacon-Johnson · Answer

@Scott Allen How long can you be under contract like this?

Aaron Zimmerman · Answer

I would probably buy a duplex then sell. You could be stuck in limbo for months if you choose to sell first. Finding property in certain markets can be difficult especially if there's a tight buy box.

Samantha Chacon-Johnson · Answer

@Aaron Zimmerman yes, but I cannot imagine having two mortage payments at the same time. Do you have any suggestion on how to navigate that?

Sell then buy or Buy then sell - which is best?

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