Typically, selling in your parent's name and buying in your LLC, under audit, may result in a disqualified exchange.

Anyways, I’m looking for someone to tell me if my strategy is flawed, sound or could be done better.....I am 30 years old, family of 5, six figure income living in a very affluent Southern California city where six figures doesn’t go far.

Typically if they really really want your project they will figure out a way to solve this issue (think Amazon).

The current market rent and price is in the agreement above… Does one typically go higher or lower than the market rent/price on these sorts of agreements?

Is this typical?

Typically, if people don't want to list on MLS during a seller's market, it means either the property is not likely to qualify for traditional financing, which could work in your favor, or they want more than the property is actually worth and can't find an agent to agree on a listing price, which could be a major barrier- you might try to see if you can find this info out.

I typically spend up to 20% of my commissions on lead generation online and off.

I don't think you typically pay points on FHA, so that might be some upfront cash savings.Have you called other property managers to see what their opinions of the property and rents in the area are?

A lot of investors overlook the deals/opportunities that are already easily within grasp of their existing portfolio.Your analysis seems apt to me, obviously the 'your time' is hard to quantify - I'm not sure that the jump from 2 to 3 bedroom would enable getting less needy tenants - at least with what we're doing - I think this would actually typically be the reverse if I had to generalize. 

Typical rentals in Highland Park for a 2 BR 1 BA run about $800-$900.