ESPRESSO TO GO:
Use the Patriot - it's durable, which comes in handy when driving through Mafia territory in Portland.
Start in Shoreside Vale and finish in Portland.
When I did it I didn't use the Patriot but I did start in Shoreside Vale after scouting out all the stands in Staunton first. All of the guides suggested starting in Portland but that didn't seem to make sense. It seemed more logical to start at the second stand in Shoreside Vale, race down to Francis International Airport, go over the lift bridge, take out the five stands and cross the Callahan Bridge since one of the stands is pretty much right around the corner. Then it was just a matter of getting to St. Marks through Hepburn Heights and approaching Salvatore's mansion from the left.
I guess it would be just as easy in reverse but since Portland is smaller and a little easier to navigate it's less stressful with the timer winding down.
S.A.M.:
This is much easier if you have four bribe stars at your hideout & a police Enforcer. After you blow up the plane, go back to your Staunton hideout, lose the Wanted Level, then finish the mission.
Thanks, I'll give that a shot. The part where I get stuck the most is shooting the plane down though. I find the best method is to just race over to the airport, take out the Columbians and then blow up the plane once it lands. Unfortunately it doesn't leave much room for error and if it doesn't actually blow up before it reaches the end of the runway the mission fails. The one time I've been successful I messed up the run back to the construction site but an Enforcer might just do the trick. Thanks again.