In many markets, I think we are are the top of the market and it gets riskier assuming that prices will simply keep going up to cover all those fancy things you want to put into a house you will never live in.

Our PM should be able to screen out the bad ones but I just wanted to know if paying for advertising to these other complexes would be worth it or if I should stick to online ads mostly.

The lessons that I learned the most, were to be firm with your rules, and definitely follow tenant screening, and don't take crap from contractors.

I have found that I haven't been able to fully cover the cost of the house based on our VRBO and AirBnB listing of the property, but it has been close so I just figure my usage, which is about once a month, I am basically paying for.Here is how I analyzed what I could afford. 

I am currently living with my girlfriend and a roomate in a 2 bedroom apartment in Santa Clara for $3,500 a month, where $2,000 of the rent is covered by me and $1,500 of that is covered by the roommate.

They may have mortgage so the price has to be enough to cover the mortgage and the taxes.

Screen screen screen is your best defense

They are already selling at below market price, they may think that covers it from their end. 

I've watched plenty of YouTube videos, I've read some blogs, and I think I have a general sense of what the process would need to be for me to screen tenants, keep up with city ordinance and state laws and so on.

3) if I fix it up and can’t sell it, can I rent it and cover my costs?