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The Clash weren’t the first to wonder “Should I Stay or Should I Go.”
But it is a question many first-time homebuyers pose to themselves in a potential real estate deal that usually will become the biggest investment of their lives.
Boston’s historic housing stock means buyers often make offers on homes that are decades —if not centuries — old. That means there is a lot of wear-and-tear and inevitable repairs to consider tackling.
When is it time to stay, and when is it time to go when dealing with drafty windows, a cracked foundation, or other signs of — shall we say, maturity?

“The current market is tough for first-time buyers,” said Eric Sugrue, a Redfin Boston agent. “The inventory of available houses to buy has never been lower in our market. Most buyers realize they will have to compromise.”
Buy a home warranty or negotiate one from the seller to provide peace of mind that at least all of the mechanicals are covered, Sugrue said, before emphasizing that buyers remember the acronym PEACH: Plumbing, Electrical, Air Conditioning, and Heating.
“It’s easy to get caught up in the aesthetic design aspects when touring a home, but it’s important that buyers — and especially first-time buyers — focus more on the things that either they can’t change or can cost them a lot of money down the road,” added Amanda Pendleton, a Zillow home trends expert.
Location and layout are hard to change, so if you aren’t satisfied with those, it might be best to find another home. But nice-to-have things like a chef’s kitchen are easier to add down the line. Buyers should look for signs of pests and structural damage: Visible water damage, uneven floorboards, and gaps in windows or doors can be a sign of problems becoming bigger issues if they aren’t fixed, Pendleton said.
While all of those interviewed for this story emphasized the importance of working with experienced real estate agents and conducting a full home inspection for true peace of mind, they also noted there’s no one-issue-applies-to-all when it comes to home buying.
“That is a very challenging question to answer, because it’s so much about personal preference,” said Sarah Gustafson, president of the Massachusetts Association of Realtors. “Each house is unique, and it’s unique to the buyer who is buying. So, it really comes down to what their temperature is for the property.”
As to that fixer-upper home?
Chip and Joanna Gaines 2.0: Come right in. Those looking for a turnkey pad? Perhaps keep walking to the next open house.
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