Downsides of Applying Late?

[PanjandrumOfReason]

I am scheduled to take the LSAT for the first time this February 2018, so none of my applications would be complete until some time in March. Other than having to repay the application and CAS report fees next cycle, is there a downside to applying late this cycle, and then simply reapplying next cycle if I don't get an acceptable outcome this cycle?

In particular, if I reject a school's acceptance this year, will they look unfavorably upon me if I apply to them again next cycle? For example, suppose my number one outcome is Chicago with a Ruby and my number two outcome is Harvard, and I get accepted this cycle to Chicago with a half-tuition scholarship and Harvard. If I reject both those offers this cycle hoping for the Ruby next cycle, will I lose points with either of them when I apply to both again next cycle?

The consensus among most of the schools I want to apply to is that they will accept my February score but have warned me that I will be significantly disadvantaged by applying so late. As a side note, my rush to apply this cycle is due to my age of 34 and my ever-increasing gap in employment history.

All comments appreciated.