Preparing for Long Term Travel

I have been working as a software engineer for a small software company in Milwaukee for the past 6 1/2 years. This plan may not have been possible even as recently as 3 or 4 years ago, but fortunately for me, my company has become a lot more flexible towards remote work in recent years.

 

UPDATE 4/14/2018 – My company recently sold me (and several others) to another company as part of a larger acquisition. Very strange situation and definitely not the best timing for something like this to happen. However, it does not appear to impact any of my arrangements to work remotely and travel, so I’m still good to go here.

This was easily the biggest decision/hurdle for me to deal with. I have owned a house in Milwaukee for the past 13 years. Here is a list of many of the factors that went into my decision making process.

There is a third option, and that would be to just keep the house and don’t rent it. This is clearly the most expensive option as I’d still be paying the mortgage and maintenance costs while I continue to have additional living expenses as I travel. I really didn’t give this option too much thought. My practical nature doesn’t see that as the best option.

That leaves sell vs rent. Even though I think the easier option in many ways would be to sell and avoid some potential headaches of managing a rental property, I really don’t think I want to sell.

I’ve always been very prudent and practical when it comes to financial decisions and I think it’s still a good investment to keep it and maintain it as a rental, at least in the short term. Also, I like the additional flexibility and safety net it provides by keeping it to potentially come back to. I can always change my mind and sell it in the future if I choose. This also allows me to dip my toe into the waters of being a landlord and owning a rental property. Something I could envision getting more involved with in the future if this goes well.

That does however leave me with a lot more work to do to figure out all the logistics of setting up and managing a rental property remotely which definitely has it’s own challenges. I will follow up with other more detailed posts about all the significant preparations and efforts that have gone into preparing my house for rent given my unique circumstances.

UPDATE 4/15/2018 – Finding a Tenant on Craigslist
UPDATE 4/16/2018 – Automated Property Management with Cozy
UPDATE 4/23/2018 – Preparing to Move Out

This is easily one of the biggest wildcards of my entire plan and a source of some headaches to be honest.

I’ve owned a 2005 Infiniti FX, now with 137,000 miles, for almost 10 years. It’s generally been a great vehicle but I’ve been telling myself (and everyone else) that I was going to buy a new vehicle for the past 2 years now. I’ve moved to the point where I don’t want to put any more money into it. However, this past fall it became disabled with a bad wheel bearing, shot tie-rods, and a broken control arm. So whether I wanted to or not I was sort of forced to spend a significant amount of money to fix it. It is now safe to drive again but could probably use some additional work if I’m going to keep it for any real length of time.

I had every intention of buying a new vehicle, but now I’m waffling and considering keeping it and rolling the proverbial dice. If I could get another 8-12 months out of it that might be ideal, given some of my longer term plans (more to come on that). But until recently, that was still quite a bit more time than I was planning on keeping it – so it’s a real question mark and a bit of a dilemma at the moment. Oh the indecision…

UPDATE 4/15/2018 – I’ve decided to keep my current vehicle. I’m getting it serviced this weekend with a complete tune-up, and also having a tow hitch installed!

As organized as I am in certain areas of my life, I struggle to routinely go to the doctor. I think I’m a typical guy in that regard. I have to be on my death bed to go to the doctor if I’m feeling sick. Even then I usually don’t. I’m making a concerted effort to have a complete physical before I leave.

UPDATE 4/15/2018 – Although I didn’t schedule a Dr. appointment, I did get my yearly health evaluation and blood draw through my employer so I am counting this item as completed.

I’ve also procrastinated for many years to get my eyes checked. I got prescription glasses and contacts in 1997 before I went to live in Hungary for a year. Unfortunately I never wore the glasses much and could never get adjusted to the contacts. I haven’t had an eye exam since!! I stare at a computer monitor day in and day out and come home from work with headaches most days. It’s gotten to a point where I have to do something about it.

UPDATE 4/15/2018 – The Optometrist laughed when I told her my last eye exam was in the 90’s. Never the less, I have 2 new prescription glasses, one for driving and distance and one for work and reading. This is going to be an adjustment for me but I’m excited to be able to see again how nature intended.

The only doctor I don’t procrastinate going to is the dentist. I don’t know why. I made sure to schedule a cleaning before I left to tie me over for at least 6 months.

I am a creature of habit and working out is part of my routine. I’d like to continue to have access to a gym wherever I am. As of right now I haven’t done this, but anticipate it will be something that I deal with after I’ve already left and am at my initial destination.

Assisting in my strategy to build up travel rewards points. I obtained a Southwest Rapid Rewards Visa card almost 2 years now and have already taken a free flight to Denver and still have around 70,000 points. I tend to fly Southwest a lot and they are adding Hawaii to their routes later this year! I just added the Chase Sapphire Preferred due to their strong travel rewards, 50,000 sign-up points, ability to transfer points to 7 other affiliates including Southwest Airlines, and other nice benefits such as primary car rental insurance, no foreign transaction fees, trip cancellation reimbursement, trip/baggage delay reimbursement, purchase protection, extended warranty, and more.

Passport, front and back of all credit cards, insurance cards, and any other important documents in case anything gets stolen.

Some added precautions with the recent Equifax breach that affected 145.5 million people and higher potential risk of getting my credit cards or identity stolen while traveling.

Among other things, I am taking with me a backpack in which I have a considerable amount of expensive electronics (2 Laptops, GoPro, Roku, Gaming headset with Microphone, and more). This is my livelihood and would be pretty bad if it were to get stolen. These locks aren’t going to stop someone from stealing my entire bag, but might deter an opportunistic pickpocket.

Even though I just had a complete tune-up to my vehicle, I still do have an older vehicle. I opted for the mid-tier AAA Plus membership. The Basic membership only allows for towing up to 7 miles. The Plus bumps that up to 100 miles. Being that I’m starting this journey with a lengthy road trip where I may be in some more remote areas from time to time I think the additional level of coverage was warranted.

I installed Prey Project app on my personal MacBook Pro. This free software will send me a text message if my laptop is turned on once I indicate that’s its been stolen. It will also gather and deliver detailed evidence back to me, including pictures of who’s using the stolen device, its current location, the wifi networks surrounding it, public and private IP addresses, and much more. It also offers some other cool features like remotely wiping data, locking the device down, and even retrieve your most important files. Hope to never have to use this but good to know it’s there if I need it.

I have a general itinerary mapped out in my head but I don’t want to fully commit to booking more than 1 or 2 destinations (at most) in advance in case things change.