If renting during the holidays / winter is difficult in your area then wait. 

Aloha,First off, 1 - 3 days "after grace period" most certainly IS late (excluding weekends and holidays). and you should confirm with prior LL that they paid the "late fee".Second, by offering lower rent to someone with apparently good records, vs. what I am assuming is market rent to the person with poor history AND an elderly, disabled person is exactly what can get you into a Fair Housing violation.

It is about the end of the year, and certainly tax is important (as yes, Holiday is important too :) ...) 

I definitely had a problem renting it during the holidays.

The holidays are right around the corner make sure you tell everyone about your new job.

Every area is different but we manage to catch visitors for every season whereas people with larger homes are usually only able to capitalize on the holidays and summer season.  

hang in there, its that time of the year, holiday and family gatherings/traveling/new years all play a major factor, especially in my area...you could try to market on Facebook marketplace or re-listing with new pictures and a different description on craigslist.

•Disclaimer I slept at a holiday inn last nightWhat problem do you solve for him by being creative in fianancing the property?

The global financial crisis has hit the native property market quite differently than the holiday home market which dominates the costal regions.If you want proper analysis you need to look at local publications, English language versions will be very Costa-sentric and will provide a pretty narrow view, 50% of the property in Spain is bought and sold by Spaniards but foreigners of various nationalities all profess to be experts in the country as a whole.

Any and all help welcome - hope you all had a great holiday!