We inherited some shady tenants that our property manager has gotten rid of and done a LOT of work to move in better tenants, but, on top of needing to be subdivided, it is currently nickel and diming us to death, plus we need two new roofs and all of the central AC units need to be replaced soon.

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.

Then look for something that you can buy for lower than the market but rent at or above the market.Also find out what a typical rehab would cost you and break it down by major components (flooring, roof, plumbing, painting, etc). 

I expected to put in about $5-8k to update fixtures and some appliances.After the Home Inspection I've got three big concerns going forward: 1) Roof hasn't been touched since late 90s early 2000s.

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.

Just want to cover all my bases. 

I did not move forward under the impression that the tenant will pay 1400/month AND cover the HOA costs.