Caroline

High season for our Guanacaste vacation rentals is mid-December through Easter. We are already getting some reservation requests for the 2019/2020 high season. In fact, we recently received a request to reserve our Condo Reeves for six weeks from late January to early March 2020. However, after much deliberation, we turned it down. Here’s why. We definitely thought long and hard about the request before turning it down because long [...]

As we build our FIRE escape plan, health insurance continues to bedevil us. Our health insurance premiums went up several percentage points for 2019, and that was enough to put us over the $3,000 mark for coverage PER MONTH. Health insurance is our single highest line item. It is higher than our monthly housing and car payments combined! If we’re going to feel secure in our FIRE escape plan, we’ll [...]

Living in New York City, the financial capital of the world, talk of the markets can easily occur multiple times a day even for the average bystander. I also happen to be a personal finance junkie, used to work in finance and still have friends in the field, so recession watch is at the top of my mind. The recent inversion of the yield curve, where the yield on the [...]

As we've been writing about on here since the beginning of this website, our youngest daughter goes off to college later this year, and that will be the moment we officially become empty-nesters and can employ our FIRE escape plan. She is now receiving her college decisions, and scholarship / financial aid offers, and so her college price tag is become more clear by the day. Private college costs $300,000 [...]

Some of the links in this post are affiliate links. We may receive compensation if you click one of those links and purchase a product. This reader is choosing between a real estate investment in Alabama or Costa Rica: My wife and I (both born and raised in the US) are looking into buying our first rental property. I'm looking at a condo in Gulf Shores, Alabama, but she wants [...]

With both our youngest daughter and my nephew graduating high school this year, the subject of taking a gap year did come up for discussion. Both kids are going straight to college, but both did express interest in Costa Rica if they had opted to do a gap year. My nephew is interested in marine biology and spent a few weeks in Spain studying Spanish, so Costa Rica would be [...]

In a recent post, Mr. Free @ 33 blogged that FIRE is a paradox, pointing out that the people most well-positioned to achieve are the people least likely to need it – Warren Buffett is the example cited. In the post, Mr. Free @ 33 was inspired by Retire By 40, another blogger who had posted that FIRE is a fad due to its anti-establishment appeal which by definition then [...]

My friend who took almost six months off for a travel sabbatical recently landed a job. He got this offer after two to three months of job searching, and it is at a comparable level to where he left off. Clearly his time away didn’t detract from his career. That said, there is no guarantee that if you take extended time away from your career you can pick up right [...]

While we have sold off real estate before, we have done far more buying than selling (19 purchases, 3 sales). However, we have a rental condo in our Jacksonville Florida portfolio that we are thinking of selling. We have made the mistake before of selling prematurely, and we have good reasons to keep this place. We similarly considered selling our Indianapolis turnkey portfolio recently, but instead opted to hold it [...]