Unlike when we are “on vacation” we knew there was going to be a lot of downtime. Our solution was to buy a couple of Roku streaming sticks. We are staying at places with two TVs.

The Roku sticks plug directly into the HDMI port of the TV and usually there is also a USB port on the TV that can power the Roku.

They recently added the ability to work with captive portals where you need to validate with the hotel’s wifi before being able to get internet access.

While I really didn’t have a problem throwing away all of my old CDs, it is a lot harder to part with both my physical DVD collection and my hoard of digital movies that “fell off the back of a truck” I’ve been collecting since 2006.

My thought process is that while all music is available on demand via streaming, movies come in and out of availability all of the time and are spread across multiple services.

My plan is to take my DVD collection to my parents house and backup my media collection to Amazon S3

Back in the 90s, Columbia House had a service where you could buy 12 CDs for the price of one.

I would refer my “friends” who all happened to live with me with made up names and “they” would get free music and I would get CDs for referring them.

Of course I had a 200 Disc CD changer.

I am now going through three 200 disc cases full of CDs from back then throwing them away in preparation for the next phase of our lives.

I haven’t listened to a physical piece of media since the introduction of the first iPod in 2001.

Who would have thought that 20 years later, you would be able to stream all of the world’s music from a watch?

While these cables work perfectly well for almost everything. They don’t support 100W charging for my MacBook Pro 16 inch nor do they support video over USB C for my portable USB C monitor.

I also bought a few of these

They are the truly universal cable.

When I am working at home. I have my monitor setup at the correct height. I hated just working with my laptop until I discovered the Roost adjustable laptop stand. Of course I use this with an Apple keyboard and mouse.

When I work at home, I have two external displays in addition to my laptop monitor.

To duplicate that setup, I use my iPad as a second display and a USB C Powered monitor as a third display.

Our next question was how do we get mail if we are traveling everywhere?

We looked into virtual mailboxes

A virtual mailbox is a service that receives physical mail for us and we can log onto a website and request either that the service open the mail and scan it for us or forward the mail to wherever we are at the moment.

We chose 1Postal.

I’ve been looking for the perfect charging /data cable forever for my combination of USB-C and Lightning devices.

I hated digging through my bag when we travel trying to find the right cable depending on what I needed. Now I can just pull any cord out of my laptop bag and make it work.

This is the perfect cord for charging almost everything, everywhere

Don’t ever cheap out and buy a Basic Economy seat.

We bought one before I knew how bad they were. Lesson learned.

This was all meant to be a learning experience before we start for real. My wife flew separately from me and I learned that even with the Amex Delta Reserve authorized user where we pay an extra $175, she still doesn’t get a free checked bag or get on the upgrade list if she doesn’t fly with me.

The only thing she gets is Delta lounge access.

We also over packed and our luggage was over 50 pounds and we had to pay $130. So I just ordered a portable luggage scale from Amazon

One thing we realized early on was that we had to treat staying at hotels like we treat living at home and not like we were on vacation. Part of that was ordering groceries and water using Instacart. We had to resist the temptation of buying food at the hotel and eating out all of the time.

We will be doing an Instacart order on the day we land. Homewood Suites has full refrigerators.

By June, we thought we had everything planned out.

We drove to Nashville, TN for the weekend.

Then we realized we hated road trips. On the way back home we decided to get rid of both of our cars, fly everywhere and take Uber when we arrived.

One advantage of staying in Hilton over AirBnbs is that between credit cards, status at the hotel, and promotions, you can easily get 20%-30% back toward future hotel stays.

I won’t go into too many details. The Points Guy has a great explanation.

We are just leaving the Embassy Suites at Icon Park in Orlando. We were here for 11 days to both take care of some business and just to try “living” in a hotel and to see if we missed anything we should be doing.

Overall we don’t have any complaints. It is just what you would expect from an Embassy. A good breakfast, a decent happy hour selection and it had laundry facilities that accepted contactless payments like Apple Pay.

We really liked Hilton’s Embassy Suites when we stay for vacations and I stay for work. You get a bedroom and separate living room, free hot breakfast and free drinks during happy hour.

But we knew they would be unaffordable to stay in all of the time. But we could afford Hilton’s Homewood Suites and they have full kitchens and two room suites like Embassy.

Once we decided we were going to be “Digital Nomads”, we wanted to see how we would like staying in AirBnbs. We stayed in one for month and realized that we liked hotels better.

We liked the consistency, the gym, the pool, the housekeeping, and the customer service of Hilton brand hotels.

We were told that although we owned the entire unit, we could only stay there 180 days. The rest of the time we had to rent it out. But we made money when it was rented.

My wife, said “well we said we wanted to travel. Let’s just stay there for the Winter and travel the country for the rest of the year staying in AirBnbs”.

After we decided that we were going to move to Florida, we started looking for condos. We already did the big house in the burbs and we wanted to do something different. We thought we had found the perfect place and we realized it was a condotel…

It all started in March 2022 with an idea that my wife and I wanted to move to a new place after staying in GA all of our lives.

We thought about moving to Florida for the weather and because it was a tax free state.

And that’s where the adventure began…