Well, say I became a CFI and started teaching. On the side I get my ME rating but kept on teaching. What is my chance of flying an ME at a freight company?
That's how most people do it. CFI until they can get hired. Some do other work such as aerial survey or jumpers, but with CFI-ing you'll keep your head in the books more. Teaching instruments would help a lot as well.
As of now, there's no minimum ME time at my company, and probably not at others as well. However, if our staffing gets better one might expect our mins to go up. I was hired with 33 fixed-wing ME.
Do I have to build time as a single engine pilot or can I just become a FO (if it is called that in the freight world) on a ME airplane.
At my company they are called "SICs," but some do call them FOs, and you can go that route. No matter what, you'll need 1200 hours to act as a PIC.
Like I said my goal is to become an airline pilot (at least now) but I am in no rush to get there. I like flying and I'd like to experience most of it.
That's a great attitude. Make sure it is something you really want to do though. It would suck if 6 months into your freight gig you realized you're losing out on a bunch of airline seniority. What if the airlines aren't hiring when your contract is up? Will you be satisfied sticking around in the freight business?
So having said that, lets say I'm a CFI with 400 hrs by this time next year. What would you recommend me doing? ie: build more time and apply? or try going in with a small freight company?
400 hours isn't a lot. And if my company's staffing issues get fixed, you most likely won't see 400 hour SIC's anymore. It used to be they required 1050 to come to class, and it
might go back that way again. Who knows.
I'd recommend building your time - become a CFI, CFII, and MEI. Concentrate heavily on basic instrument flying, perfecting your scan, and flying instruments without glass or a GPS. (Do get some GPS skills though - we do have them in many aircraft.)
I'd apply when you were qualified, and keep updating your application till you get the call. Study the gouges on aviationinterviews.com and be ready for a short notice interview.