I'm fairly confident that with modern upgrades the house will support that valuation and command high rents.

I get that these places have an old school style, but can't you recreate that with modern clean looking materials. 

But you are just using estate planning and LLC's to work in the modern era to fight modern wealth destruction (law suits/judgments, healthcare expenses leading to long term care / incapacity, remarriage after death, death or remarriage of children.) 

My career goal is to one day design and build large, modern homes and I have access to the money required through investors, but having my dad on board is my number one priority.Build a successful real estate portfolio.

Obviously if something were to happen we could be held liable in our litigious society.

It's hard to do it publicly in the modern world. 

However, Pasadena is full of older houses that need some modern amenities and features, like higher ceilings, smooth ceilings, new flooring, double pane windows, modern appliances, modern paint colors, etc. 

A house that has survived 100 years of neglect has probably got good bones, while modern construction is often all about slapping stuff together as quickly and cheaply as possible in order to maximize profit for the developer.

In announcing plans for the center earlier this year, they described the new operation’s objectives this way: “Modernizes the Army for the future… will integrate the future operational environment, threat and technologies to develop and deliver future force requirements, designing future force organizations, and delivering materiel capabilities.”The Futures Command center is expected to lead innovation for the Army’s top six modernization projects, including improvement to its tactical missile system, combat vehicles and helicopters, defense teams and weapons.Army officials indicated they were seeking a high-tech, creative culture for the location, rather than a traditionally structured Army post.

@Laura Royce give "American Modern" a call.