I have been feeding a small group of strays for some time now (don't ask how
I started!).  Group is down to 2 now after the oldest (3-4 years) had to be
euthanized because of large, inoperable malignant abdominal tumor.  The 2
guys left have both been neutered & come when I pull up when I whistle for
them!  Both are very friendly but afraid of their own shadows!  Both cats
have had someone bring them food every day have never had to hunt for their
food. (the person who started told me that they were kittens when she
started but that she couldn't catch them).

One has always been 'protected' by an older female.  His first foster mother
just disappeared one day & the second is the one who died a few weeks ago.
When he was young, he would not come out until his first 'mother' went and
got him.  After he hooked up with his second 'mother', if you saw one, you
saw the other.  She was more of a wanderer & if he couldn't find her right
away at feeding time, he would just howl until she came.  Now, he seems very
lost.  For days after I took her away, he would come out and walk around my
car, (which he usually does not do) and I think he realized I took her away
in that.  I did try to get him that day but unfortunately he got out of my
arms & was so frightened, he ran & hid.  Now, he comes down to eat but often
goes up on a ledge where he just meows & meows waiting for her.  He has
never been a wanderer & stays pretty much in a small secluded area where he
has reasonably good shelter & protection.  Its in a small marina so he is
used to people coming and going & even spends time on one of the boats on
which one person lives.

The other guy is more of a wanderer & sometimes I don't see him for a couple
of days.  He is afraid of loud noises or voices.  He comes running to my
feet when I whistle & even when I've tripped & hit him with my foot, he just
comes right back rubbing against my leg.  However, if I so much as move my
hand towards him, he runs so I can't touch him.  I suspect someone has hit
him.  There is a younger male that belongs to one of the stores there & this
guy just howls until this younger cat comes down.

The 2 strays, however, are a little afraid of each other so if one gets a
little too close they both scatter a few feet.  No fighting, a few hisses &
its all over.  I have never been scratched or bitten by either & if I do
something to scare them, they don't move too far!

Thing is I have a friend who will take the first one.  He would be an indoor
cat as they have coyotes in their area. But I think he could make it inside.
He loves to be petted, eats out of my hand, is not real crazy about being
picked up (particularly now) & I haven't tried to do that lately.   I'd like
to be able to give them some suggestions about how to approach this. Does
anyone have any suggestions I could give them?