@Jacob Stark,
In my short landlord career (about a year and a half now)- I've had prepaid rents twice already (My rentals are in a small college town in Montana). I'm happy for the guaranteed rent- but am worried about potential eviction at the end of the year if they start to not pay at that time... I'm a remote landlord- my Property Manager is required to keep the money in an "escrow" type account- I get rent payments every month just like normal...
My two prepaid rent times are from basically normal reasons:
#1 was going to school and had grants. Wanted to make sure rent was always taken care of. They left under bad circumstances. They didn't trash the place, but it was hard to get them out. BUT, I had a horrible, horrible property manager at that time that caused many of these issues...- and this was at the time of transitioning to a new property manager, so things were in flux because of the last property manager's lack of communication...
#2 received a large inheritance. They do not have a lengthy work history. They are renting now- and planning on buying a house in a year, once they are more established... As a side note, I just closed on this house about a month ago- within a week, these tenants have already planted flowers and landscaping... Pretty cool...
I think there could be many questionable scenarios as to why they want to prepay--- but potentially some good reasons also...
Anyway, my 2.5 cents- adjusted for inflation...
Jimmy