How hard is it to find tenants during fall/winter?

[Max T.]

I have all of my leases terminate or renew April through August. Demand is high in summer and my schedule is more flexible. Once I had an unexpected vacancy in October and it took me 2 months to fill. Also lowered the rent. I see decent deals come across my screen now, but if I went for them I wouldn't take possession until fall. Any experienced LLs do much renting on the off-months? I'm interested in how that works out for you.