Hi Nicole,
I am an owner of a two antenna system (91xg and a RCA ANT751).
Looking at your radar plot, I come down with GroundUrMast suggestion of testing with one antenna, then if a two antenna application is needed, invest in setting it up. I will say though a two antenna application I feel would be something if you are in it for the long term I would go for pretty quickly. The set up choice I'd go for would be a 91xg being pointed at 150 magnetic. The second antenna I would consider being a Winegard HD7698P aimed at 23 magnetic.
91xg: CW, PBS
HD7698: ABC, CBS, FOX, MyNet, NBC, PBS (ION too, it is so strong you should see it while not pointed at it)
If going after the two antenna application, I would mount a tripod on the roof with a 10' pole and mount the 91xg on the top, then the HD7698 3 or 4' below.
I would run these as separate systems, meaning coaxes come off each antenna on their own down to a A/B switch in your home and depending on what channel you want to watch, you switch over.
I would also install an RCA preamp on BOTH antennas. Place the power supply for the preamp on the lead coming into your house, just before the A/B Switch.
My system has two separate leads and inside I have my A/B switch to go between the beam and the little antenna. I have found it quite effective. My situation though, I receive most of my signals on the 91xg that the little antenna sees. The little antenna is there for VHF support and as a back up should the 91xg have any problems.
All that said, your signals for NBC and the CW are weak. You may experience a drop out or two. 2-edge conditions are a fickle thing and signals can vary. Keep your expectations reasonable. I have a red shaded 7 db signal that my beam is pointed at. 99% of the time it is reliable, but occasionally there is that whacky moment that it freezes and comes right back. Be prepared for this.
Teleview had a nice all in one solution, but I think down the road, you'll likely be happier with two dedicated antennas that each serve all the signals you are trying for. Taking a big bite with one antenna may bring many of the signals in, but two antennas allows you the freedom to really dedicate resources to each set of towers a one antenna solution wouldn't.
RE: CW simulcast of WBKI RF 19 on WMYO digital subchannel 58.3. Yes, the CW programming will be available via WMYO (magnetic 23). However, the flexibility of the two antenna system is nice to receive both signals should one go down. I enjoy that with my beam. I have two CBS affiliates at my reception.
Best of luck!