My current property manager doesn't instead sending a monthly ledger with the month's payments (company name, pay date, amount) as well as monthly income/expense statement.

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. 

While I am not an accountant, and you should speak to yours about this, there is a loophole in the tax code called the STR Loophole which allows your STR (provided you are not using a PM) to be counted as active income/active expense so that the costs, payments, depreciation etc. goes against your active W-2 income.

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.