Need some advice

[Sohrab Ansari]

This is my first post. I love the community in here. I need some help deciding. I really want to get more into investing in real estate. 5 years goal is to have 20k/month in passive cash flow. 

I bought a condo back in 2014 in Ann Arbor, MI for about 67k (cash). Rented for $1110/month for two years. The lease is about to end. HOA is about $320/month. The tenants want to renew for another year.

This was my first buy and I don't think it was an awesome buy but it cash flowed about 400-500/month. If I were to go back and know what I know now, I won't have bought this condo. 

I am thinking of selling the condo, adding more money to make it 100k, leverage to buy multifamily between 500-700k that cash flows better. Is this reasonable/possible? 

Or 

Sell the condo and use the money +  hard money to do rehabs until i have about 500k then invest in cash flowing multifamily real estate. 

a little about me: I am a doc. I have a full time job. I love learning new things and business. I want to be free in 3-5 years. I have about 350k in student loans and no other significant debt. Credit score 700-720. 

I would greatly appreciate it If you have any other tips or suggestions to get starting. Thanks in advance.