Will a tenant pay over market rents for those amenities? 

I hear that I should utilize cost segregation to calculate my depreciation in this first year of renting, but every calculator I find starts with the question "How much did you pay for the house?".

To add, if I went the real estate agent route, I would keep my current part time job at my local recreation center, making just enough to pay off my loan and monthly expenses. 

Why are people willing to pay these prices when they could put it in a CD?

Only a select percentage of renters are looking for that size or pay a premium for extra bedrooms.

We do not do flips as that is a job (granted a job that can pay well if you do it right) So we have not purchased in over 2 years.  

(I do not want to do AirBnb) So I'm okay with even paying a few hundred a month if its acting as a second home, something like house hacking light.

We are currently using RentRedi but there is a long lead time from when the tenant pays to when the money is deposited into our account...sometimes up to 10 days.

I've personally invested in Groundfloor's 10-Year Anniversary Note paying 10% interest on a one-year term.

Learn, pay your dues, gather that experience, and by the time you're a very, very young 23-25, you'll be an experienced investor.