My father doesn't make money outside of mowing for my mowing business and my mother only makes about $45k so they are unable to afford their nearly $4k/mo mortgage and are very close to short-selling their proper since my mother was just denied for a refinance.My question and topic for discussion is as follows: My parent's 14 acre farm in Northern Virginia (Loudoun County) has a tax appraisal of about $700k.

If you can find a well-performing property in San Diego that you can afford, you can invest here (you won't).

@Angela Chen IF you are able to pull the $500k out at any point after you close on the deal, and you can afford to tie up cash for a few months. 

If you can afford the repair go ahead and do it.If not try another insurance company. 

Pro's:  If you consider Chicago, LA, San Francisco, and New York the major cities in the US, Chicago is still the most affordable out of all of those (Despite property taxes). 

Figured OK, this should provide at least some indication of new affordable housing going in around town. 

I can afford the payments for the 145k mortgage pretty easily, but I wasn’t sure if that was a smart strategy or if I should be thinking differently or missing something important?

This may be a great opportunity to save up as much as possible and move to a more affordable, landlord-friendly state.

Could i honestly expect to rent the house out at $2800-$3000/month, honestly i'm skeptical because i think if a renter can afford that, they can afford to own a house?

I would think I should buy a home on the cheaper side of what I could afford to be conservative with money and lower my expenses and living below my means starting out.