As a newbie this kind of seems to be the distant future but I love to see how you plan and strategy is laid out.I have spent my career as a cost analyst in manufacturing, it's interesting to see assumptions laid out in terms of land development.

I've owned two condos in the (distant) past and rented both after moving out of them but sold both nearly 10 years ago.

Lots of distant relatives in that area and SE missouri.Thanks!

The main reason I ask this question is because my main goal is to become a buy and hold multi-family investor in a not so distant future and I want to know how a good deal looks like when I get it from other wholesalers.

You get out of a distant market into something local, you defer taxes, you likely increase your returns. 

For friends and distant family I did second liens on other properties so I could use their money like cash.  

Hi John, kinda depends on the family relationship, a distant cousin, you'll need to be a broker/agent, if it's mother, brither, sister, father ther is no problem.

Trying to make it work both as primary residence for the parents and as a cash flowing rental in the distant future might not be the best use of the OP's time and money.  

For example in a flip, you are providing a move-in ready home and if done right the buyer is unlikely to worry about the difficulty of upgrading the home in the more distant future.

Actually, this method works best when the market tanks, so you can buy low in a distressed market ... call it a hunch, but San Diego seems to be softening a bit and there is a decent chance (if you're lucky) that you may see such great buying opportunities in the not so distant future.