If the filters look good (no gunk in the bowl, etc.), why not leave them until the end of the season. All you risk is having the filter plug up when under way and having to get towed in. I am sure your wife would enjoy the adventure.
Incidentally, I had a fuel problem with my westerbeke two weeks ago. We started the engine normally and motored out of the harbor. We then sailed a while until the wind died before starting the engine to motor back into the wind. After that we sailed for about 8 miles to our anchorage. When we went to restart the engine to anchor, the engine started, ran for about 3-4 seconds then quit. I got the engine started after pumping the had pump 50 or so times then cranking with the throttle wide open until it started. We motored in and anchored. The next morning the engine again started, ran a few seconds then quit. Once again the hand pump and wide open throttle cranking got it started. After about 20 minutes the engine stopped again and I had to sail back to the mooring. The next day I came on board and changed all three fuel filters (that takes about 30 minutes). The racor and lift pump filters were fine and I assume that the on-engine filter was also OK. After the filter change I got the engine running but it shut down again after about a minute. Before trouble shooting the system further I decided to log my filter changes, while thinking about the problem. While logging the filter changes in my maintenance log, I noticed that the last logged fuel fill was last August and that we had run the engine almost 25 hours since then. A quick check through the log book demonstrated that I had not forgotten to log any fuel fills. Since my boat only has a 12 gallon tank and we typically burn about 0.45 gallons per hour, I figured we had burned about 11.5 gallons of fuel. In other words, my fuel problem was that I didn't have any. I keep track of fuel consumption by loggiong fuel changes and engine hours since I don't have a fuel gauge. It seems that my engine maintenance guy didn't fill the tank last fall when the engine was winterized. You just can't get good help anymore. I gave him a stern talking to while I was going ashore to fill my gerry cans to fill the tank. Since I filled the tank and purged the air out of the system (50 pumps of the hand pump followed by starting with the throttle wide open), I have had no fuel problems. I would fire my engine maintenance guy, but I have a soft spot for him and at his age (60s) you have to expect a few lapses of memor