For most of us, buying a house is the biggest financial decision we'll make. But buying a house is more than just a financial decision, it's also a very personal and emotional one. 

In this segment from "The Five" recorded on Sept. 1, Fool contributor Jeremy Bowman discusses a decision he made about buying during the height of the pandemic. The end result may surprise you. Fool contributor Jason Hall hosted this segment.

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Jason Hall: What is the most important financial decision you've ever made or the most important decision you made that impacted your financial future? Jeremy, you kick us off here.

Jeremy Bowman: Okay. Well, since we were just talking about our real estate and residential real estate, I'll stay on topic which is I just became a home-buyer or homeowner for the first time in July. It was a bit of a saga buying a house. My wife and I, we were living in New York before the pandemic started and we were actually in contract in February, so before everything went haywire.

Jason Hall: Oh, wow. So you were in the city, right, New York City?

Jeremy Bowman: Yeah. We were buying like a second home/Airbnb was the idea-upstate in...

Jason Hall: Got it

Jeremy Bowman: in New Paltz, which is a college town the Hudson Valley. Pandemic, March happens, then pandemic starts. We're going through inspections at this time and the markets crashed, schools are closing and everything is crazy, and it just felt like the world was ending. The only other experience it really reminded me of that time was 9/11. We had to make a decision about whether it was time to put down money for the house basically. I just got too nervous with everything going on. It's funny just to see what's happened in the stock market since then, but to me, it was just like well, the stock market's crashed. I thought the house is worth less than we [laughs] were paying. Actually, we tried to low-ball and they didn't go for it. Anyway, we lost the house, so that was maybe, I don't know. It's hard to say what would have happened if we would have bought it.

Jason Hall: But you're going, you're making that decision based on the information in front of you at the time, and you're looking at a property that's going to be partly an investment property because you're you talking about like it's an Airbnb sort of thing, and you're going into all these lock downs and restrictions and the uncertainty. Hindsight's always 20/20, but looking based on the information you have, just talk about going through that.

Jeremy Bowman: Oh, yeah, sure. I think buying a house, it's probably the biggest financial decision most of us are going to make and our biggest investment. But primarily, it's going to be a personal decision about where you're living, or even in our case, if it was going to be a second-home kind of thing. But like you said with doing the Airbnb thing, at that point, the Airbnb market was starting to pop, certainly would continue. But thinking about your own personal safety at that time, COVID was brand new and nobody really knew what to think about it, it's like, do you want to share your home with strangers? We had a baby at the time too and the answer is probably not, unless you're, you know. That definitely influenced us in that direction.

Jason Hall: Contrast that with the making the decision to buy recently.

Jeremy Bowman: Yeah. Then we came out to Maine now where we bought a house. We've been up here since October. We were living in a rental apartment for a while and thinking about buying a place. Like a lot of the country, the housing market has been crazy around here. I think in some ways, we were lucky to find a place, it was actually an off-the-market listing so there was no competition or anything to buy it. Definitely the needs-work kind of place, but we found it in April and started then and closed in July. It's a process, it's definitely a big investment, but yeah, I think it feels good to be a homeowner for sure. I was a renter for a very long time and I think it's nice. Like we were talking about control too, it's nice to have full control of your own space. There are risks that come with that for sure, but if something stupid breaks, I don't have to wait on a landlord for a week to fix it, so just that thing.

Jason Hall: You have a far more financial predictability about your housing costs, you lock in a lot about, so that's a powerful way to lever your financial future.

Jeremy Bowman: Yeah, you don't have to worry about rent increases, which is nice.

Jason Hall: Right. There we go.