<p>Let’s say you want to choose a city where you will very likely live the rest of your life, and here is the criteria: </p>
<li><p>You can do your work from anywhere, and you will do it for the next 25 years, so you want a vibrant business climate;</p></li>
<li><p>You prefer big cities; anything less than 750,000 is too small;</p></li>
<li><p>Seasons are o.k. but too cold isn’t o.k., however, tropical heat is just fine;</p></li>
<li><p>The city must contain decent universities, and at least one good hospital;</p></li>
<li><p>Public transit system is desirable in case you get too old to drive;</p></li>
<li><p>Money doesn’t matter, but, cost of living DOES matter, because you don’t want to throw money away on an extreme high cost of living city if a more average one will do just as well; </p></li>
<li><p>You want to be near water, and water sports;</p></li>
<li><p>You like a mix of cultures;</p></li>
<li><p>Has to have one (or more) decent airports, as you like to travel for fun, and, you HAVE to travel for business;</p></li>
<li><p>You want to stay near the eastern section of the U.S.; also, tropical islands are not out of the question;</p></li>
<li><p>You like places with a bit of “weird” or some unique character to them.</p></li>
</ol>
<p>I don’t think I’d pick a place that met your criteria. However, just brainstorming which cities might fit that list…I’d say Miami…and then I’d say Boston except you said “too cold is not OK” and I don’t know what is too cold for you. Another might be Philadelphia. There are likely other cities besides Miami in the south that meet your criteria but I don’t know them as well.</p>
<p>What about Washington, D.C. (although I don’t know much about the cost of living there)?</p>
<p>It has the mix of cultures, the airports, the Metro, the ocean is not too far away.</p>
<p>I guess it has a unique culture but is probably not weird in the best sense of the word.</p>
<p>I think it would be hard to find a tropical island near the East coast with a large urban population, a good university and a hospital.</p>
<p>How about someplace in Georgia or South Carolina – Savannah or Charleston, for example?.. these cities probably don’t meet your urban size criterion though.</p>
<p>It’s interesting how many have said Miami, which we (lovingly) tend to refer to as “New York South” or alternatively “North Cuba”. </p>
<p>Speaking of, does anyone live in or near New York City, and specifically Brooklyn?</p>
<p>Last, does anyone who lives in a “no withholding tax” city (Miami, Houston) who has also lived in a “tax city” think that there is some slight advantage to having no state or local taxes? Or, does it all equal out in the end, considering higher property taxes, service taxes, etc.?</p>
<p>Seems to me that #6 and #10 are at odds with each other. Personally I would pick Chicago. I was just there last weekend ( haven’t been there for 20 years) and I have to say it’s got everything you are looking for except proximity to the east. Cold is relative to where you’ve lived most of your life. I moved to Minneapolis after college and I prefer cold winters ( a thing of the past since global warming) to sweltering humid summers where everyone runs from car to air conditioning.</p>
<p>Cost of housing in many of those cities - Miami, DC, Chicago is VERY high! Not so in Houston. You can still get a very nice house for under 200k.</p>
<p>They don’t meet all your criteria, but consider:</p>
<p>Providence RI, Charlotte, Charleston, Asheville (heard so many good things about it), Charlottesville, Williamsburg/Norfolk, anywhere in Delaware (supposedly great salaries but COL is not bad at all), like the suggestion of Annapolis, Allentown.</p>
<p>I think D.C. has one of the highest COLs in the country - it’s an awesome city, but, I don’t like how it dies in August, and I don’t like the stress level - I spend about two weeks out of every six there now, and it sort of strikes me that it’s a city to spend time in to build contacts and a resume and then leave, but, it doesn’t hit me as a place to live out two+ decades. </p>
<p>Everyone I know who lives in DC now says things like “as soon as I accomplish X I can go home” etc.</p>
<p>You have a lot of criteria and I originally was gonna say NYC as a possibility but it didn’t mesh with your desire to not have a high cost of living and NYC is an expensive place to live. </p>
<p>I also was thinking of Baltimore based on some of your criteria but haven’t been there myself. Also, thought of Providence but it isn’t that big.</p>