Now that I have all the categories identified, I need to determine how important each factor is.
Step 1: The Dealbreakers
This is the easiest part. These are the non-negotiables, the bouncers at the front door of my retirement club. There’s no point in researching its property taxes if I would be fundamentally unhappy or unsafe there.
- Acceptance of LGBTQ+: This is my number one. It’s not just about laws, but about the general culture and community. A state that is actively hostile or rolling back rights is an immediate “No.”
This leaves only 15 states to even consider: California, Colorado, Connecticut, Hawaii, Illinois, Maine, Maryland, Massachusetts, Minnesota, Nevada, New Jersey, New York, Oregon, Vermont, Washington
- Proximity to an International Airport: I plan to travel, and I don’t want to spend half a day driving just to get to a major airport. This removes Maine
- Access to Nature: I need mountains or a large body of water (ocean or a Great Lake). A landlocked, flat state just won’t work for my mental health. This removes Nevada.
We are now down to 13 possible states: California, Colorado, Connecticut, Hawaii, Illinois, Maryland, Massachusetts, Minnesota, New Jersey, New York, Oregon, Vermont, Washington
Step 2: Weighting The Categories
Now, for the states that made it past the velvet rope, it’s time for the real scoring. I’ll break my categories into three tiers: High, Medium, and Low Priority.
High Priority (3x Weight)
These are the big levers. A great score here can make up for a poor score elsewhere. They have the biggest impact on my day-to-day happiness and long-term financial health.
- Taxes on Retirement Income: This is the most important financial factor for me. I have a large nest egg, but it’s primarily in tax-deferred accounts. A state with no income tax or one that specifically exempts retirement income will save me tens of thousands of dollars a year.
- Weather: This is the most flexible category. It is a high priority as a place like Maui can help offset some costs, but we have lived in Southern Illinois and survived fine as well.
- Running/Hiking Trails: This is my primary hobby and a huge part of my lifestyle. I need abundant, well-maintained, and scenic trails.
| State | Taxes | Weather | Trails | Total |
| Washington | 10 | 8 | 10 | 28 |
| New York | 7 | 6 | 9 | 22 |
| Colorado | 4 | 8 | 10 | 22 |
| Hawaii | 4 | 10 | 8 | 22 |
| Oregon | 3 | 8 | 9 | 20 |
| California | 1 | 9 | 10 | 20 |
| New Jersey | 6 | 6 | 7 | 19 |
| Maryland | 5 | 6 | 7 | 18 |
| Illinois | 9 | 3 | 4 | 16 |
| Vermont | 2 | 4 | 9 | 15 |
| Massachusetts | 2 | 4 | 8 | 14 |
| Connecticut | 2 | 4 | 6 | 12 |
| Minnesota | 1 | 2 | 8 | 11 |
I feel comfortable cutting the bottom four off the list.
Medium Priority (2x Weight)
These are very important, but I have more wiggle room. A state doesn’t have to be perfect in these areas, but it needs to be solid.
- Housing (Home Price & Property Tax): While I have the capital, I’m not looking to be house-poor. I want a good value. I’m willing to pay for a great location, but I don’t want to be gouged by sky-high property taxes that effectively act as a second mortgage.
- Healthcare: I’m looking for high-quality hospital systems and a good selection of doctors. While costs are a factor, access to top-tier care is the priority here.
- Family/Friend Proximity: Our closest relative live in the Chicagoland area and Michigan. We do have friends in Colorado
| State | Housing | Healthcare | Family | Total |
| Colorado | 7 | 8 | 8 | 23 |
| Maryland | 6 | 10 | 7 | 23 |
| Illinois | 4 | 9 | 10 | 23 |
| New York | 3 | 10 | 5 | 18 |
| New Jersey | 3 | 8 | 6 | 17 |
| Washington | 5 | 9 | 2 | 16 |
| Oregon | 5 | 8 | 2 | 15 |
| California | 1 | 10 | 2 | 13 |
| Hawaii | 1 | 5 | 1 | 7 |
Unfortunately, Hawaii, California and Oregon are gone. Washington stays because of its strong High Priority score, but New Jersey is also eliminated. Leaving us with: Washington, New York, Colorado, Maryland, and Illinois. I’m surprised New York is still in the running.
Low Priority (1x Weight)
These are the “nice-to-haves” or factors that tend not to vary enough to swing a decision. As I mentioned, a $20/month difference in an internet bill won’t make or break a state for me. These will mostly serve as tie-breakers if a few states are neck-and-neck after the other calculations.
- General Cost of Living (Utilities, Food, Gas): While important, this is often correlated with things I’ve already ranked higher, like housing and taxes. In most places I’d consider, the costs for these goods won’t be astronomically different. I can also control these costs through my own habits.
- Sales Tax: An annoyance, but it’s unlikely to be a deciding factor.
- Walkability: While I love a walkable town center for an afternoon stroll, my main form of recreation is hiking, which I’ll be driving to anyway.
- Crime Rates: I will assume any place I seriously consider will be in a safe, low-crime community.
| State | COL | Sales Tax | Walkability | Crime Rates | Total |
| New York | 7 | 6 | 10 | 8 | 31 |
| Maryland | 6 | 9 | 8 | 8 | 31 |
| Colorado | 6 | 7 | 8 | 8 | 29 |
| Illinois | 8 | 4 | 9 | 8 | 29 |
| Washington | 5 | 5 | 8 | 8 | 26 |
There is not much of a significant difference between these states.
The Winner
I took the average for each category. Multiplied High by 3, Medium by 2 and then added them all together.
| State | High | Med | Low | Total |
| Washington | 9.3 | 5.3 | 6.5 | 45.2 |
| Colorado | 7.3 | 7.7 | 7.3 | 44.6 |
| New York | 7.3 | 6.0 | 7.8 | 41.8 |
| Maryland | 6.0 | 7.7 | 7.8 | 41.1 |
| Illinois | 5.3 | 7.7 | 7.3 | 38.6 |
I think I already skewed the data to get the result I wanted. I am genuinely surprised to see New York and Maryland perform so well. Illinois hangs around because we currently live there and proximity to family. But ultimately, I think Washington or Colorado will be our future home.
