Your strategy is complicated. My suggestion is to stick to a simple strategy: buy bitcoins and hold them for the long term.
My take on this is that, yes, buying and holding BTC for the long term is a strategy that many turn as it is believed that it will pay off in the future. But I'd also not sell the crypto market short and would also suggest considering a few strong alts like ETH.
With Serenity on the way it looks to me that buying and holding ETH for the long term could increase your odds of success.
As for the tax questions, As a citizen or resident of the U.S., you must pay taxes any time you convert a coin to dollars or another coin. There are no tricks that can avoid it or delay it.
I agree, as for tax, there isn't much way around it, unfortunately, you'd have to pay it as capital gains whenever you're converting your original coin for that profit within the current tax year.