The Deed Chicago season 2, episode 4 preview: No vacation from hard work

The Deed

In Wednesday’s The Deed: Chicago episode, CNBC shows audiences yet another aspect of real estate: flipping houses as vacation rentals. But the process of the flip in “Will This Host Make The Most?” is anything but a vacation.

Sean Conlon works with Robin, who wants to turn the disadvantage of being laid off from a job into an opportunity to pursue her dream career in real estate. Making things even more interesting is that her flip house is literally next door to her own home! But convenience and a dream won’t be enough to pave the way to her goal of being an “Airbnb mogul,” whatever that is.

Robin has plenty of ideas, and the rental aspect means she also has plenty of things she’s trying to do with the flip house, because she’s trying to squeeze as much out of the place as possible. It’s up to Sean to help her sort through all of the things in her head and find out what’s actually viable. Such as can a general contractor who’s working multiple jobs at the same time really devote as much time as Robin needs to pull off her grand plan?

Check out the first 10 minutes of this The Deed: Chicago episode below to see just what Robin has gotten herself into, and Sean’s first impressions:

There’s a different set of rules for rental homes than ones flipped to purchase, which is something that Sean dives into during the course of this episode. It’s not just about how to build a great rental property; he teaches Robin (and the audience) about the hows and whys of rental management. That’s just good business; it would make no sense to show her how to build a house and not how to get money out of it.

It’s also what sets The Deed apart from other real estate shows, because both Chicago and the New Orleans edition present a much fuller picture of flipping. It’s not just about building and picking out finishes; it’s about bringing people down to earth and educating them on the real cost (both literal and logistically) of all those pretty things they think they want.

Read More: Sean Conlon was never interested in TV before ‘The Deed: Chicago’

There’s a curveball that happens about mid-way through the episode that may rank as one of the more frustrating moments in The Deed: Chicago history. It’s not quite as bad as “going on vacation and abandoning the flip” but it’s up there, and Sean definitely has the right to say he told her so (but he doesn’t, because he’s a nicer guy than that).

When viewed together with the two previous episodes, “Will This Host Make The Most” continues a theme of knowing who you’re doing business with, and ultimately not putting too much of your fate in someone else’s hands.

There’s a big difference between how Sean works with people as an investor, and the recurring theme of people who rely too much on others rather than asserting themselves. Sean’s whole point of doing this show is giving people the tools they need to save themselves – teaching them to be active, not passive. Even if you’re building a home for vacation, that doesn’t mean you get to check out.

So will Robin be able to turn her dreams into reality, or will she be packing her bags and realizing that house flipping isn’t quite as exciting as she thought it would be? You’ll have to watch and see, but this week’s episode is certainly an adventure and you’ll be amazed where it ends up.

The Deed: Chicago airs Wednesdays at 10:00 p.m. ET/PT on CNBC.

Article content is (c)2020 Brittany Frederick and may not be excerpted or reproduced without express written permission by the author. Follow me on Twitter at @BFTVTwtr.

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