Do not buy in an area where you'd struggle to sell within a comfortable %age of your bid. 

We do allow a well-trained dog, preferably large, no puppies and no breeds not covered by our insurance (vet records showing breed, age, proof of current vaccination and any required pet license).

From my own experience, I didn't like the ages of a lot of hilltop homes.

(For properties of this age, months requiring some kind of repair seemed as common as months where nothing needed to be done).b.

If your expenses are extremely low, why do you need $1mil in cash flow by age 30? 

And cash is my only asset I have been saving for two years for my dream to own 5 properties before age 20.

You should be getting AGE and DECEASED INDICATOR in your data sets as well information on relatives at a minimum.  

You're correct the replies and feedback on here are somewhat aged for the most part.

Lastly is this a good investment at the age I am at currently, or is there anything similar to this career field that is in turn a great investment. 

I am guessing this is common for the age of the house.