Ideas on tax strategies for middle-aged single folks?
I think people piss their pants too much about the subject. Basic tax strategy is: "If you owe, pay"
I regard taxes like "danger". We should always be vigilant and observant and certainly avoid danger, but quite frankly, I don't run around looking over my shoulder all the time trying to avoid "DANGER!!"
I do, however, worry about and take positive action vis a vis what I refer to as "The Big Chunks"
Worried about crime? OK, I move to a better neighborhood, or apartment building with a big locked front door. I DON'T move to The South Bronx or East LA.
Stay away from known high-tax areas if you can. NY, CA. , PA, a few others.
Move a few miles from town where property taxes are a bit lower than downtown or the "Toney White Suburbs".
As far as taxes on your investments... that's more of a Rubic's Cube. I have found it much easier and (therefor better) to not let the tax paying tail wag the investor dog. I don't do anything dissolute and get my ass into tax traps but I don't jump through any particular hoops just to "dodge" a particular tax or lower my bill by some ridiculous fraction.
The "tax braggers" are mostly either tying their own hands in order to dodge a tax and therefore letting somebody else make a descision for them OR... they are like the neighbor/brother-in-law/old High School friend who's faking it -not making it. They will tell you about the "great deal" they got on a new car and how they really "took that salesman the salesman for a ride" when they can get a genuine plastic simulated wood gear-shift knob thrown in at "no extra cost."