You mean to create a Boundary around the points - if yes then the quickest way to do that is
1) Create a Surface Model and add the points to it
2) You can set the properties of the surface to get the edge that you want (change Edge Length or Edge Angle to reduce the size of the "Shrink Wrap". You can also use Trim Surface Triangles to eliminate triangles you dont want in the edge breakline
3) Create a Surface Edge Breakline around the points based on the current settings of the surface (once you have them as you want them)
Delete the surface after you have the edge breakline if you dont need it.
There is no "Shrink Wrap" to create a Boundary line without creating a surface, and there is no dynamic shrinking or swelling of the "shrink Wrap" once created - it has to be done using the Surface commands at this time.
If the points have a Feature Description then you can use Process Feature Codes to create strings through sequential points with the same code - so in your example if I had a Code Left and a Code Right I could process Feature codes to create a line along the Left side and along the right side if those were measured in sequence from Left to Right (as shown in your second image - if they dont have Feature Codes you can use Polygon Select to select the points in a group and give them a Feature Code that you have set up in a simple FXL file (like Left and Right in this case) and do the same for the southern half points) and then have the software process the feature codes to create strings along them. (this all depends on how you measured them in the field of course - if totally random then you would likely have to use the surface method above.
You can edit the Linestring created using Linestring Editor if it is not exactly what you wanted after creation
What is the real need here - to create a Boundary line from a set of points - and you need to have an Edge Length type control to determine the degree of Shrink Wrapping - and you want some type of "Slider Bar" control which is really changing the edge length dynamically to find the degree of shrink wrapping that you want - and the Boundary is then used for what purpose (to control a surface I guess right?) or is there another need here that I am missing.
So if we added a Slider Bar to the Surface Edge Length control that you could move from Left to RIght and it recomputes the surface edge based on the slider control (rather than entering say 50 then 40 then 30 then 23 (I am good) (however dynamically remodeling a surface on small surfaces is fine but on large surfaces maybe not so easy or quick (especially point cloud based surfaces) would that better meet your needs?
Let me know
Alan