Bike Seat / bike in general question

I have posted on here about my bike seat issue, but I am beginning to think I am overthinking / or not thinking enough about how the entire bike is being used. History - I have done several sprints, and going to do longer this year, and plan to do a full IM in 2018. Currently ride a road bike no aero bars and looking for a new saddle that will allow me to get down a little lower without my leg going numb. BUT most of my outdoor training does not really allow for staying an the aero position very long due to other people, dogs, turns, whatever. Maybe 5-20 minutes at time. And I do a couple of 50-100 mile large bike group rides per year.

My current trial seat is a Cobb Randee and it seems to be a good seat and solve a lot of my issues, but I feel like I am trying to make my bike live 2 lives, which I kinda am because I cant afford a tri bike right now and honestly don't think I have the time to ride 3 (I ride a mtn bike some too). Do you guys that live double lives with your bikes set them up for "normal" road bike and deal with it for race time, or spend a lot of time on the trainer to get better in the aero? Biggest reason I ask is with the Randee I can see the benefits to being forward and off the seat, but that is not a real good 2 hour riding position while on the hoods talking to people around you, and in the hoods and talking really does not get you a ton of benefit come race day. Or will continued hours in the saddle get both seating positions better and broken in?

Does any of this make sense or are you all ready to kick me off here!?!?!?