I also transferred and affiliated.
I was 75% certain I was going to transfer before I initiated - I initiated because I was 90% sure I was ready to make a lifetime commitment to my organization. (That 10% was all about being 18 and a bit flaky!)
I considered four schools for my transfer choices - two had my sorority and two didn't. I made an extra effort to get to know the chapters at both. I ended up at one of those but was only about 50% on affiliating so it took me (and the chapter) the full allowed affiliation period to make that decision.
Now more than two decades later, I know that all my choices were the right ones - but at the time it took a leap of faith and a little bit of extra effort on my part.
Boone can say what the right choices for you but the best advice possible is to follow YOUR heart... But also use your head.