I'd prefer that instead of having to worry about electricity usage and damage to the AC from being too low too long.

I only image a fire hydrant bursting and being left alone for 4 days....and what damage can result from that.

Staying away from mold, flood damage, foundation issues or anything else that appears to be too much for me to handle the first time.How much time would I be looking at daily to be at the house to manage the specialty contractors?

You would'nt have to worry about landscape, snow removal, etc. or even outside damages like roof which can be very beneficial and typically a college student wouldnt have time to do.

Insurance however, informed me that they are cancelling the insurance because of exterior paint peeling and some damage to the bottom of the walls from water.

Nice thing is that there are two other sheds in the backyard with no reported termite damage.

We ask for the maximum deposit that our state allows (2 months) because we find that it gives us a cushion if we have to evict for non-payment of rent, or they leave the unit damaged. 

The former damage was caught early and didnt damage flooring or drywall.

If there's a high risk of damage, like environmental damage requiring an expensive cleanup, then you may want to increase the deposit to cover that amount, as well.

Remember deposits are to cover damage and for larger items you need to prorate them so budget accordingly.