...and even he said there's no way we can point a dish at the HD satellites and get anything we'd want - we really do have a narrow window. ... Also they said we HAD to get an HD receiver, which is not true either. Makes me wonder if we want to even try or stick with the indoor antenna which at least gets some reception.
I'm trying to read between the lines here. Are you currently a DirecTV customer? If so, I would guess/assume SD only with an 18" round dish. You want to upgrade your account? Or are you not a current customer trying to set up an account?
I do think DirecTV is still installing SD systems, but only for a few more days, so it may very well be true that you have to get an HD receiver (especially if you are a new customer).
There is no reason at all to get a multi-satellite dish if you are not getting HD service. Everything for SD in the Seattle market (which includes your area) comes on the 101 satellite, including locals.
I'm not sure what you are referring to with regard to the indoor antenna. That must just go directly to your TV set and have nothing to do with DirecTV service. If you have an SD receiver, it may go into the SD receiver, then come back out to the TV when the receiver is off, but does nothing with regard to what you get from DirecTV.
Any upgrade to an SD account would be to an HD account, so for that you would have to get the new dish, and new HD receivers.
With regard to having DirecTV come out first and not be able to get line of sight, then allowing a contractor to try, I don't know who told you that, but I seriously doubt that DirecTV would cover the cost of the contractor. The contractor may or may not want to come out unless they are providing equipment (new account or additions), in which case promos from DirecTV would most likely not apply. You need to be careful here with regard to what you do, as you could end up paying more both initially, and ongoing.