I think the key would lie in the early states. Polling nationally would be close in January, so the momentum from the early states would be important. I think both campaigns would know that I had no shot in New Hampshire and that I would be a significant favorite in Iowa, particularly given the caucus format. In a true one-on-one matchup, those two might be less important than usual, and South Carolina would start getting a lot of attention and would probably be a must-win for me, given the more favorable than the country as a whole demographics of South Carolina for my campaign. I think I would win the state on the strength of the Upstate and the Columbia suburbs, even if OSR would certainly win in Myrtle Beach, Charleston, and Hilton Head.
From there, I'm not sure that it would be over, but I do think the schedule (assuming something roughly like 2016) would give me a slight advantage. I would probably lose in Nevada, but the number of Southern states on Super Tuesday would probably allow me to seize a lot of the momentum, as I think I would do quite well in the South in this scenario. However, if I underperformed at all that day, I would be in big trouble, as a lot of the later winner take all (or close to that) states are in less favorable territory for me (I think I'd get crushed in NY and NJ, for example). In a good scenario for me, I would become the presumptive nominee following Wisconsin, where I would cruise to victory with the WOW Counties talk radio establishment behind me (much like Cruz, although I might win the rural areas too since OSR is very different from Trump).
My campaign would certainly emphasize the abortion issue in the primaries and point out OSR's support for abortion on demand well into the second trimester. That would certainly be a breaking point for the campaign.
One area where I think I am getting too much credit is the Upper Mountain West (particularly WY, MT, and AK). The conservatism of those parts is not really a religious conservatism at all. I might still sneak them out, but a Westerner would have a shot in those states. The only states west of the plains I would feel good about would be Utah, New Mexico, and probably Idaho.
If I won the nomination, I do think I would do somewhat better than Trump in suburban areas in a 2016-like climate. A lot of the issue in those areas was Trump's rhetoric around immigration and cultural (not social) issues. I don't think I would have as much of an EC advantage as Trump did because I would probably only lose California by 20 instead of 30, including holding Orange County. With my position on immigration and a few other issues, I would also seriously target New Mexico in the general election and would probably win it before I won Michigan or maybe even New Hampshire.
Here are my map guesses:
Primary:
(I only win CO and ME because of caucuses)
My General vs. Hillary Clinton in 2016:
OSR's General vs. Hillary Clinton in 2016:
