Likelihood of finding a tenant for Nov1, if I start late summer?

[Jack B.]

I'm moving back into one of my rentals this fall, specifically November 1st and turning my currently primary residence into a rental. I was originally going to shoot for moving in February next year but I think it will be easier to find a tenant for November since I will be able to start marketing in August, during the busy season. I would stipulate that the house would not be available until November 1. How likely am I to find a tenant for this given a Nov1 move in? I figure in September I'm probably going to still have a lot of people looking and November isn't that far from the end of September. I worry because I know it's harder to find tenants in the winter, so I want to get this right.

To top it off, the house has a mother in law apartment above the garage, which would be rented out to a tenant as well. The unit is attached to the main house, so I'd have two tenants in one house, though they have separate breakers, baths, laundry, kitchens, etc. There would likely be some noise experienced by each tenant from the other tenant.

I'm hoping it's not going to be too difficult, otherwise I'll have to try a different option. Perhaps I might have to sell this house and rethink the house with MIL apartment option in the future...

Will rent house for about $3,000 a month, comparable properties in the area go for about $3,300-$3,500 with the latter being more common.

It's a highly desirable area, within walking distance of a top school district.

The MIL would generate an additional $1,300 a month in rent.