I've been stuck with a winter vacancy before and it's very difficult to fill. you can't avoid a tenant that breaks a lease, but you can reduce vacancies during challenging months by setting your lease dates appropriately. hopefully the end of winter brings you better luck. 

I have a 7 night minimum (also a 29 night maximum) and very rarely allow 5 night stays to fill gaps and then, only in high season with very high rates.3.  

Our calendar fills up fast 9-12 months ahead of time so we have to plan that far ahead.

Josh - bummer you haven't been able to get that unit filled.

If your experience has gone downhill since the merger, it may be worth switching to a more proactive manager—even if there's a cost involved.Before making the move, ask the new PM how they plan to improve visibility and fill your vacancy quickly.

But if they don’t even bother to fill out the forms to apply, or get a basic job to make ends meet, or borrow money from family or friends/ somebody else besides you, then they can’t stay.

Since you are likely not able to deduct it against your ordinary income you will be carrying over losses.They will fill out Schedule E (Form 1040) for overall income, and Form 8582 for all of your carry over losses.

Both of those websites charge the tenants more than $25 and we require all adults living in our units to pay and fill out an application. 

Its much harder to turn a property around in 6 months expecting to have 100% of your money returned back to you - but if you focus on the right property focusing on highest and best use with an ADU add (like mentioned), in-fill/lot split, or other rehabs - then hopefully a semi-decent property like that will perform like a champ in a few years. 

Their insurance has asked me to return the month's payment for the remaining days of their rental (Unfortunately, I did not have a cancellation agreement).I am unsure how to handle this situation, especially since I couldn't fill the majority of the rental dates and had to offer discounts for the days I did manage to book.