They had to refinance it to basically kind of save the house now that everything is kind of on track she wants to renovate the property.

I use buildium which is a good value and I think the integration with tenant turner alone saves triple the hours needed to be worth the cost.

I.e. if your monthly payment on a $402k PP is 1700, you are saving 314/mo, or $3768/yr.

Currently, I have limited capital, but I'm saving up.

He has been saving his money for years and has plenty of money saved but no experience with real estate investing.

Or just keep renting and saving in San Diego where we're familiar with the area and the market (which could take awhile, while we are probably 3ish years away from investing in a Midwest market).

Ultimately you will have to sell your house at a discount. 

I would focus on saving enough money that if I had a deal go bad, then that money I saved was there to cover it. 

I currently have a majority of my savings invested in the stock market but am looking to diversify into real estate and other ventures to achieve my financial goals.

Do you save three months of vacancy for each unit and $50,000 for the roof replacement?