I put myself in the camp of those not really willing to use Bitcoin to purchase goods and services, and I agree that this is a problem.
"We have more bitcoin merchants than Bitcoiners willing to spend. We don’t need more merchant adoption, but spenders adoption." -- Saunter
I believe that, in order to address this issue, the "spend-replace" practice needs to be a no-brainer.
I used this approach a couple of times for fairly large purchaes I made. However, it meant that each time I had to complete the BTC payment with my wallet, then move the fiat equivalent of the bitcoin I spent to an exchange, then use that money to purchase BTC at a rate different from the one applied for the initial BTC payment to the merchant, then move the new BTC out of the exchange and back to my wallet.
Of course, this is very annoying and not sensible for small purchases. In those cases, it makes more sense to replace multiple BTC spendings with a single BTC purchase. However, doing this manually and on a regular basis, is going to be complex and time-consuming.
A more convenient solution would be to have your wallet automatically manage the "spend-replace" process in collaboration with services like Relai, Bittr, Bitcoin Well, etc.
After I have done enough purchases using Bitcoin, I could simply receive an alert saying:
"Threshold reached! It's time to replace your Bitcoins!
Transfer xxx EUR/USD to Relai/Bittr/Well/... bank account to purchase yyy BTC that will be received right in this wallet."
I would immediately switch to a wallet offering this feature!
What do you think? Would you use such a strategy?