Well, after spending some time tinkering with this thing and going over it again and again I don't think that the transmission is bad. I went ahead and flushed the tranny, put in a new filter and fluid of course and then TRIED to replicate the problem. Here is where i stand now. If I am on level ground and start up the truck it will go without a hitch and shifts great. In fact once it is in gear it shifts up and down like its brand new. Now, if I'm sitting facing and incline and I have to go from either park or reverse into drive it takes some time to engage and will engage faster if I let it roll a little. Same goes for if I'm on a decline and need to go into reverse. But once it engages I'm good.
So, I'm not sure what this is caused by, maybe a shift solenoid, I dunno. Either way I'm not convinced that the tranny is toast and I'm just going to drive it as is and give it a littlemore tlc than normal.
Hope this helps anyone that may experience this problem.