It isn't all that unusual to see proprietary stamps used to pay the 1898 check tax, and it is likely that if someone did it on one check, they would have done it on more than one. In the case of M.F. Riley, of Woodstown, New Jersey ,we have the evidence, and an interesting progression.
First, we have check 242, written on July 30, 1898, with two one-cent proprietary battleships used to pay the tax. It was not cashed until August 16, when the bank added a two-cent documentary battleship.
Second, Riley used a two-cent proprietary battleship on check 243, also written on July 30. There is no indication as to when it was cashed, but presumably prior to August 16 or the bank would have added a proper stamp as they did to check 242.
Riley wrote check 252 on August 10, using a pair of one-cent proprietaries, and it apparently was cashed without a documentary stamp having been added.
We know that the bank was adding proper stamps by August 16, and we can deduce that they had notified Mr. Riley on that day that they were doing so, as he wrote check 256, added two one-cent proprietaries, dated them the 16th, and then added a two-cent I.R. overprint over top of them.
An alternative scenario would be that Mr. Richman took the check to the bank and was told that the stamps wouldn't be accepted, so he returned it to Riley, who added and pre-dated the documentary revenue. However it worked, it is likely that Riley began using documentary stamps on or about August 16.
It appears that most or all of the Riley checks of this period were saved. If anyone can help fill in the period prior to check 242 through, say, check 260, it would be interesting to have a detailed record of the reform of a repeat offender.