Skip to content

Let's keep in touch

Subscribe to our newsletter for timely insights and actionable tips on your real estate journey.

By signing up, you indicate that you agree to the BiggerPockets Terms & Conditions
Followed Discussions Followed Categories Followed People Followed Locations
Real Estate Deal Analysis & Advice
All Forum Categories
Followed Discussions
Followed Categories
Followed People
Followed Locations
Market News & Data
General Info
Real Estate Strategies
Landlording & Rental Properties
Real Estate Professionals
Financial, Tax, & Legal
Real Estate Classifieds
Reviews & Feedback

User Stats

32
Posts
25
Votes
Philip Wrigley
  • Property Manager
  • Chicago, IL
25
Votes |
32
Posts

Our first STR 10 years on

Philip Wrigley
  • Property Manager
  • Chicago, IL
Posted

Investment Info:

Single-family residence buy & hold investment.

Purchase price: $177,000
Cash invested: $30,000

The Nook is a downtown Galena vacation rental we acquired as a long-term buy-and-hold investment. Just steps from historic Main Street, it benefits from year-round tourism and strong weekend demand. We enhanced the guest experience with updated furnishings, thoughtful design, and sought-after amenities, creating a distinctive boutique property. Today, it delivers consistent cash flow and long-term appreciation in one of the Midwest's most established vacation rental markets.

What made you interested in investing in this type of deal?

This was our first STR deal, coming up to 10 years ago now. It was the one that "started it all" for us!

How did you find this deal and how did you negotiate it?

We used a local agent that was "fine". Now I am a licensed broker in IL so we negotiate our own deals.

How did you finance this deal?

Conventional financing - second home loan. A great way to get into this realm!

How did you add value to the deal?

High quality furnishing and creating a memorable guest stay.

What was the outcome?

High guest satisfaction rates!

Lessons learned? Challenges?

Always check on the status of a STR license with the local jurisdiction before closing on the deal!

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Plenty - message me! I am a property manager in the local area now and love to help other STR owners succeed!