Get the 1.8khz for SSB contesting. Between that and the stock 2.7khz, you're covered for SSB.

You don't want my opinion on ESSB.

You can get the 250hz for CW, but if you ever do any RTTY (which I do occasionally), I think a better compromise would be the 400hz filter. JMO

I would rethink your decision on the DVR. For SSB contesting, you're going to need it.

A second RX comes in handy for DX chasing, but I would wait until you've had some time in the chair with the radio first. I waited about a year before I bought the 2nd RX.

YMMV