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.

The math is easy: nothing/zip/nada/zero.Conversely, if you change your tactic and start making offers at say 75-90% of list price, and actually pick up a couple of fundamentally sound properties as a result, how will that change your overall financial picture?

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.

The issue is each month I am spending more time placing invoices, pictures, and other documents in folders, all which could and probably should be automated.

Just want to cover all my bases. 

@Sam Shueh I plugged in the HOA into the calculator as a tenant expense and was going off the assumption that the tenant's 1400/month will be covering the HOA.

Assume that each home is in decent shape, competitively priced (at or slightly above voucher worth) passed the Section 8 inspection, and has plenty of pictures when advertised on gosection8.com.