Yes, I can relate to some degree.
I have a fairly accurate Excel spreadsheet that allows me to keep track of various particulars regarding my BTC investment actions.
And, I have employed a couple of methods to attempt to bring down my average BTC buy-in price, which I am sure are similar to what you have attempted.. maybe with differing budget, timing (or luck).
One tactic has been to attempt to buy more BTC at a lower price (if we can figure that out), and then the other tactic is to trade... sell and then buy again lower (if we can figure that out). I got burned a few times trying the trade method.. so I feel a bit more comfortable with the keep buying method.
Same feeling here, especially since you can end up with a ROI higher than the ATH if you are a bad trader! (and I'm one).
My ROI is already much higher than I am comfortable with... And so I learned to buy and hold.
I applied this strategy to my friends and family BTCs account (which I kindly manage) and they all have sub $600 averages (suckers!).
Yeah... if you are managing someone else's stash, then there is more pressures to be careful regarding risks and to go with what, on average, is going to yield the better results.