In any contact scenario, I would think it prudent to keep some of your resources hidden in case Plan B becomes a necessity. I would also suggest carefully considering when and where contact is initiated, and concur some careful pre-contact observation is in order.
A Flaw I see in this is If you leave anything behind You may very well write if off just as you would it being stolen since you may have no way of running back to that spot and obtaining it again without putting yourself in further danger. When someone threatens your life Im sure Your last thought would be the "proper" direction to run.
Also you just made me bring up another factor just as important as if you contact them. If And when you DO contact them How do you handle yourself and what you say. Things I personally wouldnt do Is mention What Exactly I have all together on my person. Keeping your PsP thats in your cargo pocket and that Sidearm in your wasteband Holster a secret may prove smart. DO NOT Inform them of your Path or location of your hopeful destination. They may very well Follow you and get the jump on you if they decide to stay on different paths.
Things you may very well want to think about telling them is people you are expecting to meet or people that are "not to far behind or on their way" in the same direction you are taking. Even if this is a lie it may keep this person on better behavior with the risk factor of retribution. Especially if these people are men with descriptive features/professions even if this is a lie aswell. They may think twice if you say your 6 foot ex Cop Brother isnt to far behind you. Tho This may very well be the called bluff issue as well. You would have to depend on the situation not lasting long or being far enough away they wouldnt be able to follow/find you.