Few things:
If you move in to the family rental, you don't have to work any more, effective immediately. Your assets are sufficient to generate about $30k/yr (based on the 4% rule), so your expenses are covered.
You are asking how to further reduce your expenses, and after people have pointed out your housing expense is the highest, you came back and asked again where you can trim costs. You can trim costs, by reducing housing. Move to another city, or another part of the country. With the extra savings you will have, you can fly out to visit regularly.
@ RobbyJ: It is possible if I move now I can quit working, but the thing like most people much of my net worth is tied to the market. Also I haven't set up my accounts so there is enough dividends generated to cover my annual expenses! I'm actually concerned about this area and learning more too. For example a Roth Conversion ladder is something to consider but what else can be done? So despite having 25 times my income wouldn't it be prudent to have more to cover other expenses such as insurance and future medical costs? I feel those costs typically are not considered when using the 25 annual expenses practice. Does anyone else have similar concerns or different ideas? Thank you for sharing.
The good news is that it looks like you're going to win the game, and the debate is just about the point spread.
It seems that your job is anchoring you to a neighborhood you hate, and if you move to a neighborhood you love (in your family rental) then you still appear compelled to keep the job. Just how good is this job, and why do you need it? Could you telecommute or go part time, or find a replacement job?
After reading 600+ dating profiles I think you can conclude that you're wasting your time reading dating profiles. Maybe the best approach is to keep building your casual-friends network and mention that you're still looking for "the one", but that you're not in a hurry. Don't show desperation-- the hot chicks dig happy, independent, confident guys. Your women friends (especially the ones who know you're not their type) would probably be glad to fix you up, or at least to make fun of you with their other women friends... either way the word gets out and reaches the ears of a MsMM candidate.
Everybody fixates on the 4% SWR. Too many people want:
a 100% success ratio with a money-back guarantee, or
a 3.786538% SWR, or
a 91.43245% success ratio plus an annuity for the 8.6% "failure rate", or
to uncover all the "hidden" expenses, or
to agonize about their lifespan.
That's all a waste of time. Even William Bernstein says that a 4% SWR with an 80% success ratio is "good enough", and anything over that is statistically meaningless.
http://www.efficientfrontier.com/ef/901/hell3.htmThe 4% SWR computer modeling never covered all of those variables. I don't think any current modeling can accurately cover it. However you have a huge quiver of tools that you can use for situations that the 4% SWR can't even predict, let alone overcome. You're going to start at a 4% SWR and stay flexible. You're going to:
cover your bare-bones survival budget with dividend income or a SPIA, and
tweak your spending on your own instead of blindly raising it for inflation, and
spend less when the market sucks, and
score an occasional side-hustle hobby or consulting gig, and
optimize your rental properties, and
enjoy a Social Security payout, and
stay healthy enough to avoid most of the rising healthcare expenses.
Speaking as a Hawaii resident, I don't see the ROI of converting your valuable investments into "dead equity" that grows at roughly the rate of inflation-- especially the part about spending a lot of money to get a tax deduction. How about if you invest the money in rental property (with the appropriate valuations and thumbrules) or in REITs or in equities? True, real estate investments
keep you from doing other dumb stuff with your money help you diversify your portfolio, but don't over-concentrate your net worth in something that you don't really need in the first place. Besides, hot chicks dig finding their own place with their new significant other-- or you could move in with her and sublet your place.
It's worth it to keep renting until the market crashes, and then consider scooping up undervalued real estate. Otherwise you won't lose anything by renting... except for the dubious "privilege" of paying lots of mortgage interest for little tax deductions.