Hey, it’s Doug.

When it comes to vacation home co-ownership, the line between "best decision ever" and "never again" is surprisingly thin. After hearing a lot of co-owner stories, I've found it's rarely the property that causes problems—it's the systems people use (or don't use) to manage it.

With the right approach to these three key areas, your shared vacation home can deliver on its promise without the headaches.

Most co-ownership headaches come down to just three things.

1. Communication

This is where most groups stumble first.

At the beginning, everyone’s excited—group texts are flying, decisions are casual, and it feels like things are working. But over time, it gets harder to keep track of what was said, who’s doing what, or when the next decision needs to be made.

Someone misses a message. Another person forgets the plan. And suddenly, what started as a dream setup feels more like herding cats.

The best groups establish clear rhythms from the start:

• One centralized place for updates

• Guidelines for how decisions get made

• Expectations for how quickly people should respond

You don’t need to over-engineer it, but if you don’t set a structure, miscommunication will eventually catch up to you.

2. Scheduling

Nothing creates tension faster than a scheduling conflict, especially if everyone wants the same week.

Some groups do a draft. Others rotate seasons. One even ran a lottery. There’s no perfect system, but what matters most is that the rules are agreed on early and applied consistently.

Centralized scheduling stops double-booking. It also makes it easier to leave space for maintenance weeks, use a multi-year schedule to keep things fair, and trade or swap weeks without resentment.

This helps protect the harmony of the group.

3. Finances

This is the silent killer of co-ownership groups.

If one person is handling all the expenses behind the scenes—paying the cleaner, booking maintenance, managing surprise repairs—trust can start to erode. Not because they’re doing anything wrong, but because no one else has visibility.

Groups that thrive treat finances like a shared responsibility:

• Set a clear budget from the start

• Track every expense (yes, even the little ones)

• Decide upfront who can authorize purchases and what counts as a shared cost

When everyone sees the numbers, there’s less confusion, less tension, and more buy-in from the group as a whole.

That’s Why We Built Plum Connect

Plum Connect was built to solve these exact problems, without requiring anyone to become a full-time property manager.

Here’s how:

• Calendar + Scheduler: Plan vacations, book maintenance, and block off cleaning days. No more “who’s got the house next weekend?” moments.

• Messaging: Instead of bouncing between group texts, emails, and side conversations, every discussion lives in one shared space.

• Shared Banking & Expense Tracking: Issue debit cards, assign spending limits, track expenses, and build transparency into your budget.

• Document Storage: Keep your operating agreement, receipts, and important files centralized and accessible for all your decisions.

We built Plum Connect to take the stress out of co-ownership so you can focus on what really matters: enjoying your time away.

Featured Property: North Topsail Beach, NC

This is one of the most compelling listings on the platform right now.

Tucked between the sound and the ocean, this brand-new townhome sits on 2.6 acres of coastal North Carolina beauty. You’ve got deeded beach access on one side and panoramic views of the Intracoastal Waterway on the other.

It’s the kind of place where your kids can run wild while you sip coffee on the balcony, watch the boats drift by, and finally exhale.

With 6 bedrooms, 4.5 baths, and over 2,600 square feet of living space, there’s plenty of room to host family, friends, or just enjoy the quiet.

Each share comes with 5 weeks of annual use, and the property is professionally managed so you can show up, relax, and even earn income.

💸 Projected returns:

• 8–10% in the first two years

• 12–18% over the next four

Whether you’re looking for a peaceful getaway or a smart long-term investment, this home checks all the boxes.

Previous Properties:

• Bald Head Island, North Carolina

• Navarre Beach, Florida

Next Week: Holden Beach, North Carolina

Thanks again for following along.

Also, we started a free WhatsApp Channel for Real Estate Investors interested in Co-Ownership.

Curious about something we haven’t covered yet?

Just hit reply and let me know what questions you’ve got about co-ownership.
I might cover it in an upcoming newsletter!

Doug + The Plum CoOwnership Team

P.S. We're in the final stages of closing our seed round. Interested in learning more? Just reply to this email.