I'm not sure why last year's fall overseed didn't take but it had nothing to do with not aerating. The grass grew in the bare spot because it was bare. When overseed grass doesn't take in the rest of the lawn it is likely because the seed was not touching bare soil. The time to rake up the lawn was before you overseeded last fall. Then assuming the seed was at least touching the soil, you should have used a water fillable roller (rented) to roll over the seed and press it into the soil. Then start watering briefly (5 minutes?) three times per day, for 3 weeks to germinate all the fescue seed. Mowing low before the seed goes down is a good idea, because it needs sunlight to take root once the seeds germinate.

The time to start this is when the summer heat breaks and the evening temperatures cool off. If that is late September for you, fine. I would have predicted earlier in the month. That's something you play by ear. But you don't need to aerate first, so you don't need to preplan that event and work around someone else's schedule.

Then next spring, ignore all the TV commercials telling you when to fertilize. Wait until Memorial Day after the initial flush of spring growth is over. If you want to use a herbicide in the spring, do not use a weed-n-feed product, because that would be applying a fertilizer earlier than Memorial Day. The grass does not need to be fed in the early spring. In general do not use weed-n-feed products. If you need a fertilizer use a fertilizer. If you need a herbicide, spot spray with a liquid meant for your specific weeds. Spot spraying is much more effective and a lot more efficient. There are biological reasons, too, but that's beyond the scope of this discussion.

I'm having the same problem Dave. The first picture was taken in late May.

When you cut the grass low for overseeding, bag the clippings. In general you should leave the clippings on the lawn (good organic matter) but bag them this one time. You should seed more toward the first part of September. Don't fertilize until the new grass is up and growing. Most of your fertilization should be in the fall (September, October, and then a fast release nitrogen after the grass stops growing but before the ground freezes). If you have problems with crabgrass plan to use a pre-emergent next spring when the forsythia blooms. Right before overseeding, it might be good to spot spray weeds with Roundup. It will kill surrounding grass, so be judicious but it is a quick way to take out existing weeds before an overseeding. Do the spot spraying a few days before cutting the grass low. Or leave the weeds to be dealt with later. The most important thing to getting grass seed to grow is the frequent light watering. It's every day, several times a day. If you don't have irrigation and can't be home, look into getting a timer for your sprinklers. When the leaves fall, mow them and leave them in small pieces on the lawn (might take a couple passes). They provide good organic matter for your soil.