Sometimes the Best Deal Is the Exit? SW Michigan...

[Philip Wrigley]

A few years ago, my husband and I bought a distressed property in Three Oaks, Michigan for around $325,000. The home had great potential, but years of heavy cigarette smoke meant it needed a substantial renovation before it was market-ready. Our original plan was to hold it as a short-term rental (similar to the rest of our portfolio). Although guest demand was strong, we found that many visitors viewed it as more of a party house than the quiet getaway for larger groups, which created ongoing friction with neighbors. This was never our intention, of course. At the same time, local sentiment toward STRs was beginning to shift, and additional regulations seemed likely very soon. Rather than fight the tide, we pivoted. After renovating the property, we ultimately sold it for just under $500,000 and realized a strong return, even though we owed taxes on the sale (we hadn't held it long enough to qualify it for 1031).

It was a great reminder that sometimes the best investment decision isn't sticking to the original plan, it's recognizing when circumstances have changed and making the right exit. Has anyone else had a property where the business plan changed completely after purchase? We are currently looking to sell an investment in another previously "hot" market for similar reasons.

[Andrew Steffens]

The mark of a successful investor is general is knowing when to pivot.  I would say almost nothing I have ever done was according to the original plan.  Ive sold things Ive thought Id keep forever and kept things that were meant to be flipped.