I was in your exact position a few months ago. My contract with Dish was up and my price lock was expiring. I looked at numerous combinations of OTA and OTT. Before returning to Dish I had tried Spectrum + Tivo and was not happy. (Getting the cable card and tuning adapter was a real pain). As you said, overall nothing combined all the features better than Dish.
In the end I contacted DIRT and they gave me nearly the same price for the same service for another 2 years. I think my bill went up $6/mo. To me that's worth it to keep the programming and hardware I like.
With Tivo you have to watch out for their sales. The more recent sales have been pretty good, especially for the "all in service" part which is what they call Lifetime service now. They also have sales with reduced annual/monthly service fees too. At full retail for both the units and service, Tivo isn't very competitive IMO, but the sales make up for it if you can be patient.
As to cablecars issues, that depends on cable provider. Mine is Mediacom, $1.99/month to use it, 15 minutes on the phone if the CSR doesn't know what they are doing, 5 minutes if they do. Never had an issue with them that was cablecars related, not in obtaining one, not in pairing it. Note that with a Tivo setup the Mini doesn't have service fees, not from Tivo and not from the cable company.
A little clarification. The Tivo Bolt 4 tuner models do OTA or cable, only the 6 tuner version is cable only. The exception is the Bolt OTA only version.
As to which UI, I prefer Hydra which is the current one. Yes, it is missing the Live Guide, but the older version is not getting any more fixes or upgrades.
Also the Bolt supports 4K the Roamio and older models don’t.
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Be sure to check carefully for what you want. The TIVO OTA models, weather Bolt or Roamio only do OTA. The Cable models only do Cable. (Though there is a hack to make the OTA also do cable but it isn't a great hack. It works but is iffy)
If you can get the Roamio all in (lifetime) for a good price there is little reason to spend more on the newer model Bolt IMO. And as explained by osu 1991 adding a hard drive isn't like doing it with a DISH receiver. You are adding more recording space but each recording is split between the two drives, internal and external. So if either fails all recordings are lost. I do NOT recommend adding an external drive. By doing that you have doubled the chance of a drive dying and losing everything. Much better if needed to put a bigger drive internally.
I also recommend not installing the new "Hydra" OS. It's an option but most users strongly agree the older OS is better. #1 among the reason is the Tivo specific guide set up is much better than the standard scrolling guide and it isn't available in the Hydra OS.