1- Every time you cross the limits on specifications of cables and/or repeater you are starting a "got luck" game. I advise you: DON'T. You will have a lot more headeach than it is worth.
2- Specifications for communications work on limits of signal attenuation and near end cross-talk (NEXT); once this criteria is reached in a stable basis, doesn't matter the length of the cable.
3- However, safe limits for certified CAT-5 cables are 100 meters; if you exceed this limit, you are gambling.
4- Since you are not exceeding it, you should consider other types of interference that can scramble the signal for 280 meters; eletromagnetic fields of monitors, transformers and machines can do that. In this case, I would recommend using fiber all the way or, at least, shielded TP (and ground it if possible) connecting the hubs.
5- the sequence to connect two hubs or switches should be uplink-to-standard port; if you connect two hubs via only uplink or only normal port, you need a crossover cable.
6- Standard states that should be not more then 4 (four) repeaters between two single terminal nodes in an ethernet sequence; count each hub or switch in a cascading structure as one repeater. This has more to do with the timming to repeat the packages then the mere presence of the hubs or switches, so 4 is a pratical limit.
So if I have read right:
|--90m--|---75m--|---75m--|
Server--Hub1-----Hub2-----Hub3-----Client
Link Server to a Hub1 STANDARD port with a STRAIGHT UTP cable;
Link Hub1 UPLINK port to a Hub2 STANDARD port with a STRAIGHT STP cable;
Link a Hub2 STANDARD port to Hub3 UPLINK port with STRAIGHT STP cable;
Link Client to a Hub3 STANDARD port with a STRAIGHT STP cable;
--Sedrez