As BigFella said....
(1) Assuming that all rooms have cable, and main room has sat and cable; neatly run a cable along the baseboard or under the carpet from TV2 Output to a combiner at the 2nd TV, and also connect the cable from the wall to the combiner to feed TV2 with cable and sat. If TV2 has multiple input, then skip the combiner.
(2) On the more expensive side. Feed TV2 Output to a UHF transmitter. UHF receiver at 2nd TV will feed this signal into a combiner, and cable from the wall is also feed into combiner. However, if UHF equipment only operates on channels 3 and 4, then you will need a modulator between receiver and combiner to change channel to something the cable is not using. But if TV has multiple input, you could skip the modulator and combiner.
(3) Going back to BigFella's original suggestion - instead of 2 splitter/combiners, maybe one combiner will work. I don't really know, but it seems like the following should work.
You always use two diplexers, with Sat connected to Sat, and VHF connected to VHF; however, I believe both diplexers are the same and it does not matter which one goes on which end. Therefore, the cable signal comes in one diplexer on the VHF side, goes across the single cable and comes out the other diplexer on the VHF side. Assuming on the VHF side, the VHF signal can go bi-directional, it may be possible to take the Diplexer VHF Output and feed a Combiner/Splitter, then take the other 2 connections on the combiner/splitter and connect to (a) the Receiver's TV2 Output (must be on an unused cable channel), and (b) either the Receiver's Ant/Cable Input, or the TV if it has multiple inputs. So cable signal is sent to the sat receiver Ant/Cable or main TV, while TV2 Output is sent back up the cable. If sat receiver only modulates channels 3 or 4, then you may need an external modulator to change 3 to maybe 80.
It sounds like the inside of each housing unit may have a splitter to feed cable to each room. If so, then in (3) above, this splitter may have to be swapped out, or reconfigured by adding a combiner so that the cable signal and the Receiver's TV2 Output signal can both be feed into this splitter to feed the rest of the unit.
(4) If there is a cabling distribution box in a utility room, and an HD connection is not required, maybe install the receiver at the distribution box and let TV1 and TV2 Outputs feed from this point, and use UHF PRO remotes for both TV's.
SW
A little knowledge is dangerous, and a mind is a terrible thing to waste.