Charter Spectrum package seems to have nowhere near the channels, and I mean actual channels not fillers that the Top 250 does going by their site.
I also use a third party VOIP as I see you do, something alot of people overlook and use the more expensive Cable phone.
TIVO's are hard to factor in. $900 is a alot to plunk down to have no monthly fees. Likely in the long run worth it but it drives the cost up for the first few years. I pay $17 total in fees for the two rooms, at $200 a year for DISH fees that would seem to take close to four years including the cable card costs to then get ahead with two TIVO's. I don't think it is fair to count what appears to be the cost of mini's to you since we are comparing two rooms.
I have a TIVO Roamio OTA with lifetime so that I can record more satellite channels, and because it gives the OTA channels in a room for a one time $99 cost, we don't need satellite in there. Problem is it has to last long enough to because lifetime is not transferable, I would say most units last. But the second problem is technology, I see in the forums people bemoaning the fact they paid so much just a few years ago and now do not get the new features. And maybe worse, if ATSC 3.0 is implemented in the next three or four years they become obsolete or at least as a real DVR.
If the FCC goes through with making every provider allow other receivers DISH (and Directv) subscribers could benefit in the same way. If the pricing structure with DISH remains the same for me $17 total fees I would probably stay with the DISH receivers.
I can see in the long run you could be less than DISH and who knows what will be charged by anyone in the coming years, I do feel it is fair to factor in the cost of the Tivo's. If I missed you did in factoring in the $40 difference I apologize. Overall with purchasing some equipment you make a good case for at the least being competitive, and after awhile less.... with the caveat of technology thrown in.