F1 status reinstated but expired visa. Options?

I came to the US in 2008 on an F1 visa to study BS in Comp. Sc.
Due to economic hardship, I dropped out in 2011-2012. My F1 visa and i-20 expired but I stayed on and rejoined school in 2016.My F1 status got reinstated. I am on OPT currently til Feb 2020. Was I ever out of status and did I accrue unlawful presence?

What are my chances of getting my F1 visa reinstated if I travel back to India? Can go back to India and then apply for a masters program in the US?
I was also considering going to India, applying for an H4 visa after marriage. Then exploring options to convert to F1, after arriving in the US. Is that possible?
Does it matter that I have been diligently paying off my student loans and I need to stay and work in the US atleast for some time , in order to pay off my student loan? (I had a cosigner)