I wanted to say "I'll be logged into Skype every night." So, I said 「毎夜、Skypeと つながっている つもりです。」 But now I am thinking maybe the verb tense should have been 「毎夜、Skypeと つながる つもりです。」
My sense is that「 毎夜、Skypeとつながっているつもりです。」 means (1) shift forward to each evening, and then state what I will be doing at that time in the continuous tense.
I sense that 「毎夜、Skypeとつながるつもりです。」 means (1) shift forward to each morning or afternoon, (2) state with the future tense (つながる) what I will be doing even later on that day in the evening (be on Skype). So, this feels like a double future. Does that make sense?
In summary, once "つもり" shifts the context into the future, can you use the continuous verb tense?