just do it
Shawn, you will land on your feet regardless of when you take the leap.
You have quite clearly learned how to
live within your means and really that is all that it takes.
If you wait for all your financial ducks to be lined up "just so" then, chances are, you'll regret not taking the leap sooner. The only financial duck I bothered to line up was the debt-duck. I summarily shot it
and have not used a credit card or carried debt since 2002.
I was nowhere close to your level of financial security when I realized that there were more important things in life than pleasing an employer to get a good review and subsequent pay rise or stock options or whatever and ...
dare I venture to actually write it .. pleasing the DW to get ... well you know what they say, "happy wife - happy life".
mmm, cleverest myth ever conjured by a woman.
After leaving a rather hectic career as an engineer within a hi-tech company I discovered that I have a great capacity for doing very little from day to day without ever growing bored. By very little I don't mean becoming a coach potato. I simply mean choosing some project and working that one project for however long it takes to get a satisfying result. Sometimes its a household project or tied in with one of my children's current need, sometimes its a study project sometimes its pure recreation! Contrast that with working as an employee within the constraints of a shrinking budget, increasingly more products to get to market and the necessity to multi-task just to keep your head above water. I reckon it's bliss to be able to prepare a meal for the family and then all sit at the table to discuss the days affairs. Its even better when your kids willingly assist and learn how to cook and clean up after themselves in the kitchen and the house in general.
Most commentators would say that at age 39 I quit my engineering career too early however, this bothered me only a very little. It sure bothered my DW a lot. That was in 2002. I'd always been the provider and she the consumer. My goals and dreams are quite few and are the type you can realistic save toward while her appetite is for near term luxury and spontaneous pleasures. I could never take her seriously. (
If you are reading between the lines then, yes, we did divorce about 8 years later in 2010, I think. 
Now that severance package was a real bargain!)
Here's the thing. You need to live
your life. Be responsible for making
yourself happy and count yourself lucky if satisfying this one, albeit selfish, appetite serendipitously makes you wealthy or your partner similarly happy. Of course if you have children (I have 3 surviving children) then you have very clear responsibilities toward them. Even for this, I do not subscribe to the "sacrifice my life to raise the children" philosophy. I reckon that the best role model you can be for your family is to show them a person who has thought carefully about what is important and then consistently set about fulfilling those prioritized needs even at the expense of other, more frivolous, demands placed upon you.
You mentioned a relative possibly needing a house. I think it is wonderful that you are in a position to write a check for her. If this is important to you then do it but if it is merely expected of you because of the net worth you have earned throughout your working life then think twice about your reasons for being so altruistic.
My preferred gift to my family is my time, my attention and whatever wisdom they might divine out of my conversations and my behavior. It is certainly not my cash or my earning potential. It's a cultural thing instilled by my parents probably. Having seen my father die at age 51, my first son die at age 2 and my mother die at age 73 (in that order) you can well imagine that I value the days in a year more than I value the dollars in the bank.
Some time in my 30's I prepared a spread sheet figuring out post-retirement expenses and so forth. The net worth that I thought I needed to retire was a little more than 10 times what I actually had when I did make the decision to at least take an
extended sabbatical. (
read 5 to 10 years living on savings and passive investments alone ... plus whatever income my DW decided to go out and earn) During the years since 2002 I have been extremely closely involved with my children's middle and high school years and currently university years and now have a daughter graduated law and practicing in Brisbane, a son studying sound and audio engineering in Byron Bay and a gap-year youngest son who is still crystalizing in his mind just what career he might become passionate about.
I have not fully retired. You probably won't either - you might relax at first but if you are young at heart and are mindful of your health then chances are you'll feel compelled to do something in society either for coin or for charity.
I drive a taxi a few nights a week and I have surprised myself that I am still doing so after 3 years. What I get out of that "job" is interaction with lots of interesting people. I've probably acquired more "street smarts" as well! Most of my living expenses are covered by just the tips that I receive so the majority of my income from fares is all cream. Indeed saving money is much easier when you truly know how to live within your means.
Now that my kids are young adults (I still have one to get started in college) I am shifting my focus toward a long-held dream of living aboard a 40-50 foot catamaran and cruising lots of interesting places. I have assured my family that there will be nothing left in the bank for them to inherit unless, perhaps, they can salvage the boat because I am quite certain that I will kick the proverbial bucket whilst blissfully making passage between some exotic locations!
The road has been bumpy, to be sure, but I would not have it any other way.
Good luck with whichever choice you make.
