If I got a total insurance payout for everything i've got, here's how I'd go:
7D - Probably add a bit of cash and get the 5D3. Definitely KatzEye.
EOS 3 - Why didn't I buy one of these sooner? Definitely replace.
EFs 15-85 - put the money towards 5D3, I rarely use the zoom anyway, primes are fine.
Samyang 35/1.4 - Definitely get again (new not 2nd-hand next time)
FL 55/1.2 - Maybe get again, or another variant like FD55 or SSC (whatever EdMika has a kit for at the time)
85/1.8 and 100/2.0 - Probably stick to one or the other, money saved towards 5D3
70-300L - Definitely get another
430EX mk1 - Try get a 430EXII, otherwise no complaints.
Lensbaby gear - replace the whole lot (except DG Muse, got a Control Freak so don't need it).
Kenko Tubes - Definitely get again
Kenko 1.4 t/c - try to get the Pro300 DGX next time.
Takumar 50/1.4 - Probably don't need to replace, FL55/1.2 does the job
Helios 28/2.8 and Ozeck 28/2.8 OM mount - only cost $10 each
OM bellows - probably try to get EF-mount bellows next time.
Paragon 300/5.6 - only $10, why did i buy this in the first place?
30/3.5 Zodiak fisheye - get another
2x 50/4 Flektogon - get one MC version
MIR 65/3.5 - replace with Zeiss MC Flektogon 65/2.8 instead
Biometar 80/2.8 - get MC version next time
Volna 90/2.8 - too similar focal length to Biometar, ditch.
MC Biometar 120/2.8 - definitely replace
Sonnar 180/2.8 - THE 6x6 portrait lens, definitely replace, MC if possible
Jupiter 250/3.5 - probably don't need this, try replace with Ziess MC Sonnar 300/4 or get a Pentacon 500/5.6
2x Arsenal 2x T/C - Probably don't need 2 teleconverters, but they were damn useful shooting the moon, so maybe.
Filters and Tripod Stuff:
Probably get the whole lot again, except for the Tiffen 72mm and 58mm CPLs and UVs, they sit in a box and their resale value is approximately nothing so haven't even bothered selling 2nd hand.
Definitely B+W MRC UV 67mm for the 70-300L, other lenses are cheap enough so don't need protecting.
I like my Heliopan 72mm CPL and Kaesemann 67mm, the Hoya HRT 77mm is too colour-casty, won't get that next time.
Tripod and ballhead and arca-swiss plates and nodal-ninja, get the whole lot again, no complaints.