Need advice! ( This is going to be a lot so bare with me)

Wife and I live in Chicago and have a combined income of 253k ( approx 12k-13k monthly)and are expecting our first child in February of next year. Currently we own a condo in Chicago that is 2 bedrooms and 1.5 bathrooms. We pay $2k in all housing cost monthly ( principal, interest, insurance and HOA) our utilities are typically an extra $80 to $120 . Seem more below!

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I think living with your in laws sounds nice in theory but personally think it will drive you crazy after a while.

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The house is honestly big enough that we would not see each other much. It is 4 floors but I agree.

What would you do with the condo if you buy the house? Sell it? Rent it out?

Do you have cash for the house down payment without selling the condo?

I mean, if you are already under contract, then you’ve already made the decision.

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Good point we could try to rent for $2200 and put on the market. The unit is in good condition. We just replaced the water heater 2 years ago etc..you are making good points. We will try to sell

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We are currently under contract for a home in a good suburb 15mim drive from downtown Chicago at 550k 6.375% interest FHA loan and 26k down. All cost included after Principal , interest, HOA and insurance is $5k monthly utilities are estimated an additional $100-$200. The home is nice and we want it because we intend to have my wife’s parents and another baby live with us to assist with child care for foreseeable future. It has 4 br and 4bath and is spacious so would be big enough. Only issue is that I noticed the home was bought for $465k in 2022 which means we are almost paying $100k more. I am positive we are in a bubble so buying this is definitely making me pause. This is not a forever home but we could stay there for 5-10 years. We have 3 options

1. Buy the home
2. Rent a property big enough for us ( would be approx $3.5-5k a month)
3. Stay where we are and hire someone to come help ( I expect that would be 2k-5k a month)

My wife is too pregnant/sick to discuss this. My family wants us to buy the place for selfish reasons. Another point to add is that if we buy the place we would also be supporting 3 other people ( grandparents and niece) we would receive some help if we ask but I don’t expect much. After closing we would have between 20k-50k ( $20k in a brokerage account and $30k in HYSC)

We are 29 and 27 btw! Please help open to all advice!

I don’t think we are in a bubble. Did the prior owner do something to improve the home. That’s a big gain in Chicago since 2022. In five to ten years it’s unlikely you will lose money and in the time rents will increase. What makes this not the forever home?

No harm putting it on the market though for a really good price and seeing if we can get some cash.

Buy what you need, don't look back. Is it 20k over market? I have no idea, maybe. You can go nuts looking for the perfect deal, but you found something reasonably priced that you like... just go for it. At your income I don't mind saying that 20k just isn't a big number to be worried about anyway.

Every market is different, but I track real estate and it's well known that prices are rising, sometimes very quickly. I'm not concerned by what I see here, so I'd say that 85k over 3 years isn't a red flag-- at most a quick eyebrow raise and a shrug for me. As SPM1 says, it's extremely like to continue to go up in value.

Don’t think we’re in bubble. I’m curious which burb you’re buying in whether it’s over priced or not. Paying 550k for something in like Maywood or Broadview I’d be concerned vs buying in oak park.

You need to either stack reserves or earn more, taxes are likely to increase and it’ll be devastating when it happens. My profit got crushed on my rental when city raised their taxes a year ago but i made sure i had enough profit so i was ultimately fine. Sounds like a good reason to charge 2.5k for the Andersonville condo. If taxes become unaffordable worst case you sell the condo. Sounds manageable but you just gotta be ready to pull the trigger when you get into the red or once you see the writing on the wall.

If you can comfortably afford the payments and have secure jobs go for it. You can always refinance if the price goes down as well. With the rates still a bit high I think it’s a good move.

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