If you want a second, your personal income, excluding income from the property, will have to be able to sustain both payments.

Regardless what you choose, if you are the top producer in any of these fields, then you will be successful and make the money you want to sustain your lifestyle.

Can you sustain the losses?

How do you collect rent in a sustainable way when a tenant lives right next door to you? 

If you want sustainable income close and then rent it out.

then,  hold it another few years (assuming you can sustain the maintenance and any negative cash flow) ...If you are struggle with the maintenance and suddenly got nervous about negative cash flow, then sell it. 

If you are speculating on appreciation that is a viable option but you will need to contribute cash out of pocket to the monthly income to sustain the purchase.

Hmm...do you think your market can sustain higher rents?

Just make sure that it cash flows in a good market and at least sustains the mortgage in a bad market (this lowers your risk).

I am planning on getting involved in real estate, business, and subsequent investing (multi-family) as soon as I turn 18.However I was wondering if you had the chance to start over with real estate or business, what path would you take in order to generate the most money in a sustained period of time, and what steps would you take to acclimate that equity.