Turning Our Forever Home Into Our Ticket to Italy

People think you should always be happy. Good luck with that! Life happens. Other people happen. And sometimes those two things collide in spectacular fashion. 

1. A great sense of humor 

2. A willingness to go along with most of my plans 

Within reason, of course. 

Skydiving, bungee jumping, and rock climbing are all a hard pass. (Notice a theme there.) 

But renovating our home so that when I retire from teaching in six years—yes, I am counting—we can rent it out to snowbirds or corporate relocations for a few months each year? 

That one he agreed to. 

The plan is simple in theory. 

For about three months out of the year, we rent our house to responsible adults looking for sunshine. During those three months, we travel. 

First stop on the list: Italy. 

It’s beautiful. 
The food is amazing. 
The art and history are unbelievable. 

Honestly… take me now. 

And just like that… the plan was born. 
 

The Forever Home Problem 

Here’s the thing though. 

I love my home. 

We’ve lived here for nearly 20 years. 
We raised our children here. 
My grandson is growing up here. 

We’ve hosted family holidays, baby showers, birthday parties, and more gatherings than I can count. 

We’ve rented apartments before, but this is our home. Every time I think about selling it, I get a little sad. 

This is my forever home. One day I hope to pass it down. 

So, I needed a plan that would let me: 

• Live in Italy for a few months 
• Pay the mortgage while we travel 
• Keep the house 
• And do it all with a little style 

Because if nothing else, I’m a little extra. 

Why Not Airbnb? 

I don’t want our house to turn into party central. 

If there’s going to be a party at my house, I want to be the one hosting it. 

So, the idea became longer seasonal rentals instead of short weekend stays. 

Snowbirds. 
Corporate relocations. 
Traveling professionals. 

People who want a comfortable home—not a party house. 

Enter My Advisor… Chad 

This is where AI enters the story. 

I asked my advisor for help. 

I call him Chad. 
(Chad = ChatGPT.) 

Now Chad has great advice most of the time, but he can also be a little too optimistic and effervescent. I often must remind him: 

“I’m a realist. No blowing smoke.” 

Still, he’s been incredibly helpful when it comes to planning. 

Because let’s be honest… 

I am under no illusion that my house is a palace where people will pay $1,000 a night to stay. 

If you want to, I won’t stop you. 

I might even allow a party. 

Just don’t break anything. 

So I needed a way to leave… without ever really leaving.