If the property operates at a loss he eats all of it.

One at 8, then another at 9am etc) and you can get all your guys in there to place a bid on one day vs eating up your time over a week.

Unless I was 100% sure I did not lose the rent, I would eat the cost.  

If you use up all the return then inflation will eat at your capital and your 600k will be worth a lot less than today.

I agree with Carolina E., at my main job we do not end leases in November or December due to it being harder to get tenants in when it's cold.

I'm working towards my first flip and I'm trying to determine if an addition would eat my profit or be a good investment.

Make sure you eat breakfast at the garf.

If they damage the property, you pretty much have to eat the cost.

Or should I wait for more appreciation and hope increasing rates don't eat into my profits?

Your point of keeping the last month's rent at it's original amount and eat the difference is interesting, as far as I know other landlords in my areas are requiring the last month's rent gap to be paid although some kept the SD the same.