My car payment is pretty reasonable ($366/month) so that wasn't in my original plan and eats into my cash for furniture/incidentals. 

As @Michael Baum suggested, the amount of work doesn't change with the seasons, nor does the length of stay, as @Theresa Harris mentioned.My question is... in order to compete with lower total trip costs from other listings (often resulting from lower cleaning fees), should I eat a part of the cleaning fee in order to have a lower total trip cost?

But he still must eat and if he comes home to the door and starts munching the tuna maybe you can grab him then and scoot him inside?

People eat it up.

You need an Eat what you Kill mentality if you take this path.  

If that syndication doesn't work as well as you hope, then you're eating interest.

Would you offer higher, like $450k, and just eat the water and electric until the leases renew and you can adjust that out? 

So if we underperform the pro forma and we end up losing up to $100k on the deal, he would share in that $50k loss and I would eat $50k of the loss.Is that what you mean?

I have a good income producing job, however, I have a 6 member household with teens, preteens, and children who are eating up my house like Pacman, lol. 

Please be careful, at higher amounts leveraged, the carrying costs/time value of money can eat you alive if you have any hiccups in your project.