Hi Schmaks,
A long tale, so feel free to cut to the last paragraph.
I cant advise on the choice of OTA but I have been pondering upgrades after a couple of years from starting to take pictures through an 8inch Newt to where I am now, a fairly well automated system still using the Newt and but a modded DSLR. On the way I aquired a WO66 refractor, and ASIAir (I gave up on this and it lingers in a cupboard) and it all sits on an HEQ5 Pro. I live under Bortle 8 skies so I need a lot of integration time. And hands up I like galaxies, so I need reach. I have a set up I can polar align using Sharpcap in 2 minutes and then go and sit on the sofa in the house, program in a sequence of exposures and targets for the night and go to bed. I get up in the morning and its all very neatly parked. Sounds neat, however every step of the way has been a mission, so many nights of nothing, months of scratching my head, seeking out answers from the community, and general pulling hair out. Then we get to processing, don't mention processing! Where to go from here? Camera, mount, OTA, software? My setup is right on the weight limit for the mount, and I should upgrade, but on the whole I get good guiding (as long as there isn't a breeze, but I am usually tucked away from the prevailing winds). So that can wait. A new OTA? To get the reach and aperture is going to set me back £2000 for a second hand OTA and flattener. Software - I don't have the time at a good time of the day (job and a 2 year old to look after) to try to understand Pixinsight so I use Startools and am just starting to get results, but that has sent me back to my rig to understand where a myriad of issues thrown up by the better processing. However I need a few more months to get comfortable. So how do I get bang for buck? First up improve my current OTA to the best it can be, £400 or so (change the focuser, flock the interior, etc, etc) so that it is delivering the best possible image. Then for the next step a mono astrocam is going to make the biggest difference at around £1-1.5k. Lots to learn but at least I know what the rest of my kit does - even better would be a colour astrocam, get that integrated, understand that and how it effects the set up. Then move to mono (probably loose nothing on the OSC assuming I get it 2nd hand). Get that sorted. Then upgrade the mount, to an EQ6 R Pro, that will carry anything I can ever likely afford, then when I am flush go for the long fl triplet. All that is probably a 2 year plan for the first two steps, then whenever for third step.
So a long story, but slow steady steps so you have some idea as to what is working, and what needs fixing, but the idea of changing everything all at one go looks like a brave step, and is going to need a lot of patience (even more than the normal astrophotography head banging experience!).
Whatever, enjoy your deliveries and clear skies!