There are more sharks in the water for the smaller cabins because more people can afford 150k vs 350k.

I had it inspected and found that the roofers had swept all of their leftover debris to the center and tiled over it, this caused water to pool and the underlayment to eventually fail.

This will give you more time to expand your business and develop a more refined system to focus on finding more deals.

If you've got your receipts scanned and attached to transactions in your bookkeeping system, you ain't going nowhere.  :-)The reports are the awesome sauce.  

Who gets the money left after the mortgage PITI and water bills are paid?

I also think the school system gets a bad rap, because people only talk about Menlo, Paly, and San Mateo if you're not going private.

You did not mention the age of the property  you are looking at and that could make a difference if anything might need special care today like asbestos, lead paint, and the major draining system. 

This is how many went 'under water' or had more leverage than the value of the property during the great recession.Many portfolio owners with plenty of cash will maintain leverage between 50-75% as a safe play.

Look into the Profit First system.

I don't really have a support system (hence i've been on my own since age 14) so I go out seeking opportunities on my own, and calling various people for advice.