then rent out each room where possible3) Buy an apartment with little to no HOA (hard), and rent out by room to save up more to make the next step.

If it's a standard step down, you may take a big hit on points.

@Caleb Rehg  I would advise your first step is to search this site for college student rentals and student rentals and read all you can. 

I guess I can keep it as a STR and push my way through, it would just be nice if it was something that worked for someone right now and helped me take a step back for a bit, and go back to STR when I have more ability to keep up with it!

I love how you reframed failure as a stepping stone to success.

Yes, that depends if the “Step Up”rules still exist.J.

You also want a point of contact that knows underwriting too, that way they are proactive in ensuring your deal will get to the closing table.

If so, are there any steps I need to take that would allow this to happen?

To network and connect people that can add value to each other.I'm am glad you are taking the right steps and I can't wait to see how you grow your portfolio from here.

I think all the other seasoned investors would agree the best timing to make your first step into REI is yesterday.