I thought I read something over on the DISH boards about an attempt to start phasing out SD in a few years. Does this ring any bells? Has anything similar been indicated for DTV?
One of Directv's VPs made a couple (unofficial) statements in 2012 suggesting that 2016 or 2017 would be the date when SD was gone, but I imagine that is one of those things where whatever date they may have in mind it is far more likely to get pushed back over time rather than staying where it is.
Considering the lead time they granted for phasing out the MPG receivers, any movement to phase out SD will be pretty well known and won't take anyone by surprise. Since they still perform new SD only installs for customers who only want SD, they haven't even taken the basic first step of ceasing to install dishes that aren't capable of receiving the HD satellites, so I wouldn't hold my breath.
I have even less knowledge about what Dish may be up to, but I expect the situation is similar. Both companies have a lot of SD only dishes and a lot of SD only receivers out there, and until natural attrition reduces those numbers to a manageable level, the plan for phasing out SD will remain at least "a few years" out there.
Either way, it doesn't help you with your problem of not having LOS to 99W. There's not really any way around that, if you don't have LOS to that location you can't get HD on Directv. Dish has a much wider satellite spacing, so given the photos you posted I'm sure they're not an option either. If you want HD, you'll probably have to go with cable.