Currently house hacking with 2 roommates but I am looking to purchase my first true rental property.

Now worth $650,000Step 5: Brought the four family rents up to market rate which is $5200 per month.Time to complete: 10 years.Cash flow went from $350 per month to $2,000 per month.Properties are now worth around $1,000,000.Success story BStep 1: Bought a condo in 2014 in a HCOL city for $200,000 and rented it to a roommate (house hacking). 

I have been looking for properties to purchase, so  that she can live there for the school year with one or two room mates.

I quickly observed the tenant had a dog, a roommate, and an Olympic weight set - none of which was allowed per the lease.

I'm currently living in Hoboken, but my landlord is not willing to allow me to terminate my lease early, find a replacement , or sublet while my roommate continues to stay here.

Figure out your boundaries and look for the best candidates who can be your roommates.

I will be married by EOY and i don't think we'd be down to live in a house with 3 roommates haha. 

I expect the property to appraise for 300k after renovations.After renovations, I plan to find a roommate and rent one room for $800 a month and split utilities or $900 flat.

I believe that the easiest way to move forward is to buy a SFH and get a roommate or 2.

Ok yeah that sounds good, also to answer your other question, the first units rent is for a roommate, I can rent out of the rooms in my unit