Meeting Topic: Insurance & Risk: Protecting Your Investment from Flip to Rental to STR
Insurance is one of the most critical—yet often overlooked—components of real estate investing. While investors carefully analyze purchase price, renovation costs, and projected returns, insurance is often treated as an afterthought—until something goes wrong.
The reality is simple: the cost of having the right insurance—or the consequences of having the wrong coverage—can dramatically impact your profitability on both rental properties and flips.
This month, we’re bringing in an expert to break it all down.
Guest Speaker
Jackson Kysar
Agency Owner – Kysar Agency
Licensed in: NC, SC, WA, ID, MN, WI, MD
What We’ll Cover
This will be a practical, real-world discussion designed specifically for investors. Bring your questions—these are some of the key topics we’ll dive into:
Flipping Properties
- What type of insurance do you need during a flip?
- What happens if a property is damaged while vacant?
- What are the risks of DIY work or using unlicensed contractors?
- What happens if a worker is injured on-site?
- How are major losses (like fire) handled?
- Real-world scenarios: what goes wrong—and how proper coverage could have prevented it
Long-Term Rentals
- What type of insurance should landlords carry? What add-ons matter most?
- How can you secure the best rates and maximize value?
- When should you file a claim—and will it impact your future premiums?
- What does your policy not cover?
- What protections are essential for landlords and property managers?
- Can bundling multiple properties lower your costs?
- Should you be concerned about non-admitted carriers in NC? What are the risks?
- Which companies are known for smooth claims—and which are not?
- Understanding adjusters: independent, company, and public—when should you hire your own?
- Real-world lessons: how proper insurance (and permits) could have prevented costly mistakes
Short-Term Rentals (Airbnb/STRs)
- What type of insurance do STR owners actually need?
- What coverage options and endorsements should you consider?
- How do you get the best rates without sacrificing protection?
- What gaps exist in standard policies?
- What coverage is essential for STR owners and managers?
Big Picture Discussion
What is the right balance between risk and insurance?
How do you decide what to insure—and what risks to accept—when you can’t cover everything?
This is a must-attend meeting for anyone flipping, renting, or operating short-term rentals. The right knowledge could save you thousands—or protect you from a devastating loss.
Don’t Miss It!
As always, expect great networking, investor connections, and practical education you can apply immediately.
We’ll see you Thursday night!
Please register in advance so we know how much food to order.
~Coastal REIA Board
Guests: $25
Active Military & Students: FREE with valid ID
Active military and students with proper ID are admitted to meetings at no charge.
Coastal Carolina REIA is a local, non-profit organization and the only SE North Carolina affiliate chapter of the National Real Estate Investors Association, connecting investors through education, networking, and support both locally and nationwide. 