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.

[Jack B.]

Originally posted by @Krystallin Baker:

How successful you will be will be largely dependent upon a variety of factors, some you have total control over, some you don't. How well are you marketing your property? Make sure you list it out across multiple websites, not just one place. How good is the location? Not much you can change about that, but something to consider. How accurately have you priced it? Make sure you do your due diligence in choosing the right price point for both units. 

Best of luck! Seems like a feasible goal if you do your legwork! 

I usually post via Zillow Rental Manager, which posts to about a dozen sites. I also post on Craigslist.

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.