I knew a 3000 square foot house with 5 rooms would be cheaper for me than the standard 3 bedroom 1800 square foot house.

There are a lot of ways to get your foot in the door, it will just take some effort. 

To get my foot in the door I am looking at duplexes in B neighborhoods and/or properties that need some work.

The second is an 1100 sq foot condo in one of the best buildings in town but it has no view while the first unit has a spectacular view, like mind blowing view.

I fully intend to rent out several of the rooms, possibly in a Short Term situation through AirBnB type sites, some rooms to what I hope to be my daughters college friends that have Mom & Dad to foot the bill for them :) Aside from that using a small MultiFamily is a great idea as well as even doing a live in fix and flip, these are all ways to house hack and unless you just can't stomach having "roommates" or living next door to your tenants then I just can't see a downside. 

We ended up selling them this land for ~$13k and it was originally purchased by us for ~$3k (based on what we paid per square foot for the lot).

Since this is a major operational transition for me, I want to get it going on the right foot  and will probably return with more questions :-)Thanks!

A lot of people have issues keeping up with the paperwork side of things, so if you make connections and offer to help get stuff scanned and filed you may be able to get your foot in the door that way. 

Pretty new at this but as I go through listings in Los Angeles, I've started to really pay attention to the price per square foot (and the lot size too).

I know some micro-units are being built now but there aren't many to buy and, on a per square foot basis, they're extremely expensive.