Good Luck and please let us know how it turns out, I wish I had been as smart as you are at your age Call your parents and thank them!

My goal is to build up enough cash flow with adding additional rentals(15-20 rentals paid off) to one day being able to afford a vacation rental and renting that out until I’m at retirement age.

If the vast majority can't handle it, and their average age is 20 years older than you, the odds of you making it are extremely slim.I hope you educate yourself on the job and the costs and that it works out for you.

I would like to do the same thing (retirement aged and high % of equity homeowners) but was curious as to how you found these people.  

Louis is a very mixed area and we know nothing about the age of the buildings, or location, or condition, or neighborhood.

But unfortunately (or fortunately, depends on how you look at it) my old age and wisdom kicked in and going to jail and lossing my family is not worth a rent house.So basically I think we broke every rule of being a land lord possible.

I don't split up repairs and turnover replacements personally, but I'd suggest estimating these based on the age/condition of the units. 

I haven't driven by any of the properties, but based on their age and location (C/D neighborhoods), I'm expecting there's some deferred maintenance and other needed repairs.

Married to my wonderful wife for 16 years and we have two boys ages 13 and 15. 

I would like to have a clear picture of my taxable income before the end of the year as I would like to pull as much out of IRA's and place into Roth's now to reduce the impacts of minimum distributions on the IRA's at age 70 (6 years from now).So the rental income and depreciation is important to approximating taxable income.