3) I would take this opportunity to REdesign the lease and expire the lease in summer time when rental rates are at its peak instead repeating again (12-month lease) in winter time to allow tenants play this game on you in their advance.After reviewing these, you should have a good idea about the lines and should help you find a direction.I would keep tenants if they are good and takes care property well. 

We have two condos in Kihei, Maui, so even though the winter time is the "high season," we are still able to keep our units full the rest of the year too.

But I don’t think it will be very, if at all doing in the spring/winter time.

In the winter time, the rental market declines quite a bit and you can't get as much rent, and vacancies last much longer.

Your primary rental "Swanson" will of course be the winter time, 3-5 month terms, of course which is when you'd want to use it too.

We were voted number one ski town in the US the past two years so winter time is crazy busy.

  Snow/Winter time can be very misleading for how safe/quite a neighborhood is.  

Is it just normal for winter time and is expected to pick up through spring?  

I plan on keeping a side job for the winter time while I remodel our second unit.

The demand for housing really drops off in the winter time.