If I don't do this, then I risk the amount being paid as rent falling further and further from market each year which means I need to either raise rent dramatically after years of not raising them for a particular tenant (which never goes over well), or waiting for the old tenant to leave so I can establish a market rate for a new tenant (which can take along time).

It would dramatically increase my return #s but would damage my quality of life.

If anything other than cash is used as the down payment, like a seller-carried second mortgage or some “credit” for work already done, the size of the loan that the typical hard money lender will make will fall dramatically, probably down to the 55% LTV range.

If rents have increased dramatically, then it is a landlord's market.

I just don't want to feel like I'm being dramatic with the situation I'm given since I'm a contractor and definitely not trying to stay in my current career forever.

If interest rates were to increase dramatically over the next 10 years, I believe cap rates would also increase.  

The scale has been tipped on paying debts off dramatically at this point though, haha.

People have dramatic responses to traumatic events all the time.  

It's an additional cost that can change dramatically over time, and you rarely get your money's worth for whatever it's supposed to cover, and you lose complete control over your investment. 

Sometimes, I find that new clients get bad information on rental rates, either from a Realtor trying to close a deal or a neighbor who dramatically inflates the actual rental-rate.