First off, an example of thinking more in line with what you are thinking is being pursued by the Moscow Patriarch, seeking to train evangelists and missionaries. And on that same topic, there are missionary societies such as the IOCC that seek to evangelize. Why now and not earlier?
It is also important to look at the history of the Orthodox and the persecution we have suffered: in Muslim countires, evangelization of non-Christians meant death usdually for the neophyte and the person helping to convert the other. Even in some 'Christian' countries, Orthodox missionaries were put to death (St. Peter the Aleut, for example---and I'm not trying to cast stones at your church!). In countries that were already considered "orthodox' there was little need to formally missionize people, so it really wasn't on our radar screens.
In this country I've lived in two communities where the Orthodox were considered only one step above African-Americans in the informal apartheid of American society (one mayor in 1920's Indianapolis,a Klansman, ran under the promise that,if elected, he'd 'run all the n****rs and Greeks out of town'. He kicked out the latter but not the former). Here in B'ham, the club many parishioners use as a reception hall did not allow Greeks in through the front door until the 1970's--- up to the 1960's we could come there only if we were there to cook or clean.
A similar situation occurred in the United States with the growth of the Catholic church. While communities were established by immigrants and those fleeing injustice, the missionizing in this country didn't go full force until the immigrants were more accepted by society (It eventually became OK to be Irish, Italian, etc, and the children of the immigrants were educated enough to articulate their message outside of the initial cultural group). Basically we're getting there now---my own parish just celebrated their 100th anniversary, and we are waaaaay older than any other Orthodox parish in town by a factor of 4 or 5.
Otoh, one way to look at missionizing is that of the four EO communities in Birmingham, AL, there was only one that existed 35 years ago. One formed just last year and there's talk of another forming in a few years as well!
Plus, let's face it---many Orthodox were horribly catechized. Most were unaware that there really is a palpable difference between the Church and those of other groups who yearn for the Truth but were unaware that the Spirit resides among those that society despised. So you had a terrible brew of lay ignorance and societal discouragement.
Regarding the Antiochian agreement with the Non Chalcedonian Syrian Orthodox Church: my understanding is that the communities are so intermixed that both church hierarchs basically just got tired of the bickering about who was snatching who's sheep. They just agreed to keep the other where they were, which is defensible especially when considering how close the Chalcedonian and Non Chalcedonian Orthodox apparently are, based on the statement of hierarchs and such.
Just my $.02. I'm sure it'll be castigated by many, but there ya go...