A quick background on the situation:

My wife and I have had cats around for several decades, but when we
lost our "special kitty" at a ripe old age of 20, three years ago, we both
vowed that we would never get another cat because the hurt was more
than either of us could have ever imagined.
Well last year, around mid-November, a friend was having dinner with
us and asked if we were ever going to get another cat. We said "maybe
someday" and explained how we never went looking for a cat, every cat
that's ever owned us has come to us in one way or another. We must
have been tempting fate because the next day my wife called me over to
the window and out by the tree, under the birdfeeder, was a young black
cat, kind of skinny, watching us through the window.
We have "relationships" with some of the neighborhood cats (with homes)
and sometimes feed them, so we put some food out for this new cat. After
running to the corner of the yard and waiting for us to go back in the house,
he slowly approached to food and ate, and ate, and ate some more.
Long story short (or at least less long), since then his comfort distance
got shorter, we played with a string, he let us pet his head, he came over
when ever we brought food, we invited him in the kitchen to eat and warm
up (cold New England winter), put a towel in a box so he could have a
place to nap in the kitchen, let him nap on the carpet in the hallway, let
him join us in the living room after he stopped being jumpy about the TV,
and today..for the first time...I had a cat jump up onto my lap and take
an hour nap while I listened to the stereo (he seems partial to Jackson
Browne). As you might have suspected, it's beginning to look like we've
been adopted by another cat.
But here's the dilemna, he may not be a stray/feral. His schedule might
indicate that someone might have some control of his comings & goings.
Generally, it's evenings on weekdays, a long daytime "kitty visit" on Sunday,
and usually he does not visit on a snowy or rainy day. My wife's checked
around our neighborhood and nobody knows if he's somebody's cat.
Our experience has always been with female cats and , honestly, I am
awfully weak on the habits and psychology of male cats. So , finally,
here are some questions.
How much distance will a male cat cover in his wanderings, a neighbor
has said that they can cover a radius of up to 3 miles, is this true?
We could use some guidance as to how much of a search for an
"owner" is enough.
We've been talking about getting him to the vet for shots and, eventually,
neutering. Leading to an indoor, pampered life.
BUT....he's still a very jumpy cat. He's gotten past "freaking out" in the
house when startled, but we haven't been able to restrain him in any
way, such as "kitty hugs" or picking him up, and there's not enough
Iodine and Bandaids in Massachusetts to patch up the scratches if I were
to try right now.
I can get him to walk into a cat carrier using treats, but if I closed the
door.....well I'm not sure how he'd react.
Any comments as to how to get him to the vet without major trauma
would be appreciated.
How would a vet be able to handle him if he gets scared and tries to
bounce off the walls?
Should we be in the examining room, or let the vet handle him?
We're just starting to get his trust and I'd hate to mess things up now.
Any advice as to how to handle him when we got home from the vet?
Let him outside? Lock him in the basement (with one of us with him,
of course). Is he likely to not return if we let him out?
The past couple of months he's been allowed to come in and go out
as he pleased. I suppose we should try a cat box with him, first, so
he's familiar with it if we do incarcerate him after a trip to the vet.
What type of health risks are my wife and I facing, here? I've gotten
a couple of nips on the ankles (he started tackling my feet and nipping
for a while until he learned "NO", play?...testing dominance?). I've
had a t/d shot in the last 10 yrs and my understanding is that rabies
is not a worry if the cat is healthy 5 days later, but are there other
dangers from a feral? Scratches? Probably a little late to be asking
this.
He's grown, put on weight, and looks quite healthy, BTW. And the
little guy is fiesty as hell.
And what's the deal with the spontaneous swipes of the paw when he's
enjoying a head and neck rub?
Anyway, this post has gotten longer than I anticipated. If you've read
this far, thank you for hanging in there.
If you have any advice as the how we should handle this situation,
thank you again.
If you haven't guessed by now, we've become quite attached to this
kitty.