not sure how to handle feral/stray

Hi all! This is kind of a long one, so bear with me. 

Last January, my boyfriend and I started to notice a little black cat hanging around. We live on a duplex cul-de-sac with little car ports and he was often on the porch of one of the unrented duplex's or in our carport. I'm an avid cat lover so I started to feed him and did a little research.  His ear has been tipped so I'm assuming he's been part of a TNR program, but the thing is, I'm just not convinced he's feral.  He won't let us touch him and if we move too quickly he definitely bolts, but when we feed him he rubs against the wall, meows, and doesn't mind if our hand is within 2-3 inches in front of his face. He also makes VERY bold eye contact, which I've read isn't typical of a feral cat. Also, if we're 'late' feeding him he jumps up on a chair in front of the window and will chirp and sniff our more curious cat. They've also rubbed their faces against each other through the screen (which I've since discouraged since I don't know about his health...) We built him an insulated shelter with an outdoor heating pad for the winter, and I would be happy to keep our relationship as is (we already own 2 cats and 2 dogs) but I'm starting to worry because we will be moving to another state in May of 2014.  I just can't imagine leaving him without knowing he's ok. Because he's so timid, I think trapping him and taking him to a shelter would probably end in him being put down because he's so shy and the trapping/shelter atmosphere would probably be traumatic and wouldn't make him any friendlier. I also am reluctant to bring him into our home because we will be leaving the state for three weeks in December and we take all of our pets with us so I would need to find him a reliable house sitter to keep up a solid routine so we wouldn't go backwards in terms of socialization. 

I'm also wondering: how does the vet handle a checkup if the kitty is scared to the point of being dangerous?  And if the vet tells you the cat has fleas (which I'm assuming they will) how on earth are you supposed to apply flea meds to such a shy cat????

So, basically I'm stumped. Ideally, I'd like to bring him into our family, but I just don't know how to approach this, especially because I worry that moving him cross country in 7-8 months would be traumatic. Any advice would be excellent. We've been at kind of a stand still for 8 months now. I've also just read so many things about feral cats being a lost cause in terms of indoor socialization that it makes me nervous to proceed, even though I think he might not be technically feral.

Sorry for the crummy quality pic, it's through the screen!

I shall try and write later on, now Im in a hurry.

but others may step in, there are many very knowleable and active forumists

Good luck!

You need to make a plan as you have taken on responsibility for this kitty.  First decision - is he coming with you when you move?  If no, you need to find him a new home or caregiver now.  If yes, you need to decide if he will accompany you as a member of the household or as a new outside cat.  It is NOT impossible to rehome an outside cat.  It's difficult, but do-able.  If you make that decision, we can help with tips and advice.

If he's coming inside, get him to the vet now.  The vet can apply the flea meds - that will take care of the initial problem.  Most cats don't care for going to the vet anyway, so vets are used to dealing with all types of reactions.  Let them deal with that.

Have him combo tested (for FIV and FELV).  You will have another decision to make if he's positive.  Whatever decision you make, you are doing it because you want the best for this kitty.  We can all give advice about this but it is your decision.

Hopefully, he will have a clean bill of health and he turns out to be your new best friend.

Good luck and thank you for caring for him!

Does the cat have an ear tip missing or is it just the way it looks in the photo you posted?

I've taken in two outdoor kitties in the last 8 months and my parents have one that was an outdoor kitty as well and all three are amazing pets and get along well with our other animals. I'd try bringing him in since that's really the only way to see if it will be what's best for everyone.

I felt so anxious all of the time when we weren't sure what to do with the two we took in but once we got them to the vet things just sort of fell into place. Just make sure if you do bring him in that you take as much time as needed to introduce him to everyone in the house. I have found that both of ours are well adjusted and not freaked out by our other cats and dogs, it's the other cats and dogs that have been slowly getting used to them lol.

Hina our female we have had in for a few months now has only been around our dogs for three days and they are all getting along great which surprised me lol. You mentioned that one of your indoor kitties would rub heads with this outdoor boy through the screen so they must not mind each other to much though it could be different when he enters into new territory.

As far as taking him to the vet, I wouldn't worry as the vets are used to dealing with all types of animal behavior. Best of luck to you, please keep us updated!