Im willing to do whatever takes, I guess my biggest worry is that when expenses arise I wont be able to cover them.

I have my LLC set up, a rough outline business plan and will be joining my local REI but as far a taking the plunge I'm suffering from the infamous "analysis paralysis" when it comes to finding deals and making things happen.

Most MF properties rent does not cover outgo unless you have adequate down payment. 

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.

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.

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

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

I would live in the basement and rent out the other bedrooms to cover the mortgage.