When were the major systems and structure components updated (HVAC, roof, electric)Once you answer those and are comfortable with the answers from the other guys questions, you should be good. 

If after all this you sill don't feel comfortable you could have an appraiser take a look. 

Make some improvement for comfort of tenants which added value to the high rent.Completely redid second floor unit into an open concept, new kitchen and fresh paint.

While we will follow where a deal takes us, we also want to be comfortable with where we're going to live. 

creating an LLC for each property sounds like an administrative nightmare.Imagine having 10+ checking account numbers, 10+ debit cards, 10+ checkbooks, potentially 10+ tax returns...etcLook for the right fit of properties within 1 LLC where you feel comfortable with the exposure.Consult with an attorney.

I have a seller who as agreed with me on price/terms however they are older people and are not comfortable using DocuSign or other online methods.

You just have make sure your sister, or whoever else, will be comfortable with it.

We would then be responsible for paying him for the equity on the property (140 payments of $1k/mo)2) We want to maximize cash flow on the property, and my best guess is rent will be $1700/mo3) The house will likely be used to pull cash out to finance another real estate purchase in the future since we will most likely have between 65-100% equity in the house.

Purchase a duplex in San Diego and live in one unit - PROS: essentially get help paying my mortgage via rental income, proximity to rental property, maximizing FHA loan on a more expensive property (maximizing my down payment in a low interest rt environment) CONS: The market is so unbelievably expensive and rents are not comparatively high enough to really make most moves profitable, high Debt to Income ratio thereby limiting my ability to purchase again2.

Can anyone recommend an agent in this area comfortable working with first time investors?