SEPTEMBER IS SECOND CHANCES. That is what it is, agronomically and practically, and I say this as a man who has farmed in Wisconsin for fifty-one years and who has missed the August window on more than one occasion himself, in the early years, before I understood that August was a month that departed whether you were ready for it or not. September, by contrast, gives you a grace period. Not indefinitely. The frost does not care about your schedule. But September is a month that, if you understand how to use it, will let you correct the errors of August before winter makes them permanent.
With that established, here is what needs doing.
On the tulip bulbs: Now is the window. Specifically, now through mid-October in this latitude, which places you comfortably in the zone for a spring bloom. Bulbs planted before the first hard frost will establish root systems through October and November, go dormant through winter, and emerge in April. The question I receive most often about tulip bulbs is “how deep.” The answer is two to three times the diameter of the bulb, which is to say: for a standard bulb, six to eight inches. Do not be tempted by shallow planting. Shallow planting produces bulbs that heave in a hard freeze. You will plant them in September and dig them out of the lawn in December. Go deep. It is always worth going deep.
A note for those of you who are new to Wisconsin gardening specifically: the clay content of Great Lakes soil varies considerably by location. This town sits on a mix of glacial till and sandy loam, which drains well and warms quickly in spring, which is good for bulbs. If you are planting in the amended beds around the new houses, your drainage is likely adequate. If you are planting in low spots near the lake, you will want to amend with sand and compost before going in with bulbs. Water that sits will rot a bulb from the bottom up, and you will not know until spring when nothing comes up where you planted in September.
On the second coat of exterior paint: You know who you are. The coat you put on in June was fine, and it was enough to get through summer, and you told yourself you would do the second coat before fall. September is before fall, technically, for another eleven days. After that it is fall, and the temperature differential between day and night becomes problematic for adhesion. Paint applied when nighttime temperatures fall below forty-five degrees is paint that is going to peel. September 22 is your last reliable date. That is eleven days from now. I am not telling you to do it today. I am telling you when the window closes.
On the gutter: The dripping gutter that has been dripping the same drip since July is not a structural problem yet. It is a fastener problem. The gutter has pulled away from the fascia at one or more attachment points, which is causing it to hold water at the low point, which drips. The fix is two screws and forty-five minutes. The consequence of not fixing it before winter is ice formation in the low point, which will pull the gutter further from the fascia, which will become a structural problem and a several-hundred-dollar repair in March. Two screws. Forty-five minutes. Do it this week.