Gyroscopic Investing

With long term treasuries going down, do you think I should buy on secondary market now or should I wait for the November auction for the new issue? I have no experience buying on secondary market, but in my understanding it's never better, right?

Right now:

30-Year 3.875 08/15/2040 98-06 / 3.98 -1-03½ / .064 10/15

I don't think it matters.

Do whatever is easiest for you.

The bond market is highly transparent and liquid.  This means the price of the bonds pretty accurately reflects what it is worth at all times.  I think it is fine to buy either primary or secondary, and the price you pay should be extremely close to the actual value of the bond based on yields.

As I understand it, Harry Browne recommended buying bonds with a 25-30 year maturity date and selling them before they are 20 years to maturity.  FYI, the bonds I purchased on the secondary market are UNITED STATES TREAS BDS 4.37500% 11/15/2039.

I seem to comment on these old posts a lot, but perhaps because there is so much here and I am but a padawan in need of knowledge.

I've been purchasing 5/1/42 3% bonds lately. Let's say that hypothetically in 6 months the rates get up to 4%. If held in a taxable account, is it more worthwhile to purchase the 3% vs. the 4% since the premium/discount to face value is already accounted for? I'm assuming the premium/discount doesn't take into account whether you keep the bond in a taxable or non-taxable account. I would think a lower coupon option would be better, everything else equal, because you'd then be paying a premium to get a higher percent which means interest taxed as ordinary income. Since the bond portion is more about capital gains, would the 3% be the wise choice?

I realize this falls apart if you said that let's say you had rates go up to 4% in 4 years and the choice between a 2042 3% bond or a 2046 4% bond. The 3% might be less taxable gain due to lower coupon but you'd be purchasing a new one sooner (6 years since it is 4 years old versus buying a fresh 30 year bond).