First, I agree with all your points above but have to correct you that there has been a Oxford - Gatwick service before, which was run as part of the original Virgin Cross Country services to/from Brighton.
Admittedly, the paths are no longer there but if you are going to have a Oxford to Gatwick service, I feel that it should be part of a regular XC service from Brighton to say Birmingham, Manchester or Glasgow. But that is never going to happen now.
If was not for the fact that Grand central will get the 5 Class 180 trains, I would say that 2 or 3 of those should be used on the stopping service, after the arrival of the Hybrid class 800's between Reading and Oxford.
Yes, XC used to link Oxford and Gatwick but the question under discussion here is a potential point-to-point service via Reading, Guildford and Redhill, not the former intermediate journey possible on long-distance services mainly routed via West London. The paths for those along the GWML and down to Brighton are long gone, so, as you say, no chance of them coming back.
Class 180s on stopping services? Not happening. They are slow to load and unload, especially with just one passenger door on the driving coaches and a big step up and down. In addition, FGW/GWR had a bad experience when they put 180s on some Oxford semi-fasts after their return in 2012, with the effects of frequent stops and starts between Didcot and Reading thought to be pulling down mechanical reliability badly by comparison with the HT and GC sets that spend most of their time cruising along at speed up and down the ECML. Hence the switch of a set from an early Oxford-Paddington semi-fast to a limited-stop Newbury-Paddington
The use of a 180 on the 17.18 Paddington-Oxford - and an HST on the 17.36 semi-fast - is down to their ability to run at up to 125mph on the fast line to the first stop at Maidenhead and the lack of any more suitable stock for these jobs until the 387s arrive.
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My suggestion is for just an interim measure. My chain of thought is that running turbos on Oxford to Paddington sstoppers during the peak once Didcot to Paddington is electrified would be a waste of turbos, but that through services between Oxford and the stations to Reading need to be maintained. I then thought that there would be benefits to combining the services with the North Downs services rather than terminating at Reading even if the Oxford stoppers only avoid Paddington during the peak. Compared with your idea, mine has the potential to offer many useful through services for the cost of one additional turbo being required.
But as I, and JN114 have both said, once you give people the idea they can do Oxford-Gatwick direct, taking it away again two years later is not going to go down well - if you are going to do it, then do it properly - which requires electrification throughout as a minimum and preferably better infrastructure as well to address at least some of the intermediate points of conflict and potential delay that JN114 identifies.
And of course it would be a waste running Turbos to Paddington once the wires are in use - which is why it is not going to happen. While maintaining the direct link into Oxford for intermediate stations in the Thames Valley would be nice, well-organised electric to diesel connections at Didcot - where, as noted above, most semi-fasts already stand for seven minutes or so anyway, so ample time to step off one train and straight on to another - would not be the end of the world as an intermediate measure.
A fair few people commute into Didcot anyway from both directions to get to work at the likes of the Milton Park business estate or the Harwell Science Centre, using the onward bus links, so for them a Class 387 from Paddington and Reading only going as far as Didcot Parkway or a Turbo just doing Oxford-Didcot would be fine.
One additional Turbo? Perhaps for an Oxford/Banbury-Didcot shuttle, in addition to the sets already allotted to Oxford area work post-electrification. But to allow for semi-fasts linked to the Reading-Gatwick route, I somehow doubt it. A round trip for a semi-fast between Reading and Oxford typically takes 50 minutes each way, plus the time to go into the sidings at Oxford and then cross back to platform 1 for the return journey, so two hours seems a reasonable allowance to complete the exercise. i'm no diagramming expert but that looks like it needs several Turbos to maintain a 2tph frequency - and preferably make allowance for a 'hot spare' set to step up if there is disruption south of Reading that mucks up the timetable.
And that pair of two-car 165s will need to be at Oxford anyway, even after wires reach Oxford. What you are suggesting requires more Turbos to remain in the Thames Valley for longer than necessary and three-car sets at that to meet the requirements of Reading-Gatwick, when three-cars are desperately needed around Bristol.
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The Class 365 refurbishment programme is ongoing and will be completed next year, before units were planned to be cascaded from Great Northern.
Plenty more work will be needed before GWR can use them - new livery, whether paint or vinyls, and seat trim for starters, plus CCTV equipment and in-cab displays for driver-only operation, plus Dellner couplings, so they and 387s can can attach to each other for rescue purposes if a train fails.