See example below: DSCR < 1 Principal + Interest = $1,700  Taxes = $350 Insurance = $100 Association Dues = $50  Total PITIA = $2200  Rent = $2000  DSCR = Rent/PITIA = 2000/2200 = 0.91  Since the DSCR is 0.91, we know the expenses are greater than the income of the property. 

Our goal is to (eventually) have a second property where we can spend time at our retirement, and that can generate some income as a short-term rental for a portion of the time when we're not using it. 

If don't need construction funds can just do a bridge loan no income and no doc with 30% down for upto 24 months interest only 

This would reduce the capital basis for that individual in the LLC but will not be considered taxable income.

At 18 I would focus on income, saving, learning and having a strong foundation. 

I am responsible for a pretty large mortgage payment and only my employment income to pay my mortgage in all the bills.

However the property is still under my name, Do I have to report taxes for the SM LLC (which has its own EIN) that technically has no income?

You can get another income producing area of the house and it still be separate. 3.

Our plan is to hold long term (10+ years) and likely pay it off in 5-10 years to act as supplemental retirement income which we plan to get to with a couple more properties paid-off in Tulsa eventually.Would you pull the trigger on these two properties based on our goals?

Finding good income generating properties does open up some creative financing opportunities but it's good starting out to stick to a comfort range.