If you want to buy a home and live in it for a few years before renting it out, I will look at low-money down conventional/FHA options; if you cannot qualify conventionally with your DTI, I would look at DSCR loans.

Or maybe you end up doing all the renovations and management while your princess of a sister does nothing but spend the money on new shoes.Better to be your own man and make your own path.

I’d recommend getting terms from private and hard money lenders.

Are you looking to lend your money directly?

As a broke college student I can’t do much when it comes to money but I do have something even greater, time.

If it's sporadic,  IMO it will appear slimy and that the landlord just all the sudden thinks he deserves more money.  

As long as you can later prove that this money did come out of your pocket, no issue.As far as your logistics question, let's flip it and consider it from the buyer's side.

You can make money either way, just in DIFFERENT ways and on different time lines. 

Of course they don't have money now But your money will come from escrow when it closes. 

Which I don't do and I still get them coming sometimes.Just be aware once operator stars  options to refinance will only be private or  commercial loans tried myself and no luck hard hide is a assisted living with people in it heard of some doing some crazy stuff but hate going illegal on things like this, ended up refi with commercial forget about cash out and such, and you are bound by appraisal as a commercial property which was in our case 25% lower then if we sold it empty as a residential home.