Suddenly there will be a momentum... because if one property is cash flowing (say) $4,000 a year, 6 would cash flow about $24,000... and that is enough to buy a house a year.You are already on a faster path  with Flipping - which acts as it's own spring board.  

Rather than paying down your student loans faster, assuming they are at a low interest rate, save that money for a down payment for a rental.

I would like to build a castle with a modern twist, designed in mind for maybe 30+(eventually more) luxury rental units, by the water, great ammenities such as a farm to table restaurant which caters to the resort and cabanas, would like to make it more profitable faster by saving on construction by utilizing my network of friends and pros, long lasting green artistic construction, with attracting the highest paying exclusive guests in mind.

I would like to build a castle with a modern twist, designed in mind for maybe 30+(eventually more) luxury rental units, by the water, great ammenities such as a farm to table restaurant which caters to the resort and cabanas, would like to make it more profitable faster by saving on construction by utilizing my network of friends and pros, long lasting green artistic construction, with attracting the highest paying exclusive guests in mind.

I don't want to carry that time commitment or mental weight that takes me away from more productive things. 

If you are making extra payments, and therefore getting down to 80% LTC faster, you must formally write the lender and request that PMI be removed once you hit the target.

But the way I see it, people driving for dollars has no time or interest doing this way, rather make money faster with a quick flip or wholesaling.

And relevant experience with the City and dealing with Contractors can be worth its weight in gold making the project run smoothly.

Right now I would not recommend chicago area at all I’m no professional but as a life time resident of Illinois I can tell you right now is not a good time to be buying property there new taxes are coming out very soon on property, gas , cigarettes and many other things that are going to be having people run even faster the they already are.

I’m torn between thinking I have to stay at this high stress/low paying job for 2 years just to meet that requirement or pursuing my career in brokering mortgages to kickstart and really ramp up my capital savings to obtain my house hack that much faster.