Sam,
I've been in real estate for almost two years now so only a short period of time. I would recommend buying a single family house or a duplex and house hacking like you mentioned in your post. I have been renting from my brother and sister in law waiting for the right opportunity (paying $425 a month). My friend and I just purchased a duplex on the north side of Holland for $300,000. One half rents for $1,620 a month and we are going to occupy the other unit. Its technically 3 bedrooms and 2 bathrooms each side but we are going to finish off the 4th room and 3rd bathroom as well. We are going to rent to two of our friends and they will be paying about $300-350 for a room. So basically my friend and I who purchased the duplex will be living for about $100/month not including vacancy, repairs, maintenance and we will be self managing since its only one unit. I think that living at home is also a good option since it is likely free but if the right opportunity comes up don't be afraid to go after it!