Am I being too conservative?

Single Family Home (1-4 Units)

Small business owner in a HCOL (Chicago). I've owned a 2-bed starter condo since 2021, but my longer-term goal has always been to owner occupy a small multi-family to generate some rental income. I want it to be my long-term (if not forever) home, so I'm extremely picky about unit configuration and location. I'm happy where I am so not really in a rush.

A few weeks ago, a property came on the market that checks just about all of my boxes: perfect location, exactly what I want for an owner unit, two other units to rent that are in pristine condition, leases up right around when I'd close. It's as close to ideal as I could ask for. Only problem is it's overpriced. I submitted an offer that my agent and I felt was fair and competitive and the seller responded with a "thanks but I want my asking price." It's been a couple weeks now and they haven't gotten any other offers. Average time on market for multifamily in this neighborhood is five days, so that tells you a little bit about the price they're asking for.

The thing is, I could afford it at the asking price. It would be cash flow negative for the first few years, but with projected rent increases of 2-3% (pretty conservative for this neighborhood), it would go positive in year 4. Granted, that's without any major unexpected expenses, but I would also have some cash reserves leftover after the purchase, and the building was gut renovated in 2013 and has been immaculately maintained, by all accounts, plus had some capital improvements in the last few years (obviously inspections would confirm).

I can also swing this purchase without selling the condo. I have it at a great interest rate, so it can easily rent for around 2x my monthly payment. That gives me some more cushion.

So far, my agent and I have been sitting tight. The fact that they aren't getting other offers reinforces the notion that this property is priced too high, and we feel like they have to budge eventually. But the stalemate is wearing on my nerves, and I don't want to lose this property. Reading through this sub also has me reconsidering whether being cash negative is really the red flag I've been treating it as, especially when it's only for a few years on a home I'll also live in long-term.

Obviously I have some emotions tied up in this, so my head isn't as clear as it should be. What would you do?

Posted Jul 4, 2025, 1:18 AM UTC

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