Investing is not a way to get out of debt it is a method used to make your money earn it's keep.

However, The San Diego market is much more difficult to get involved in.

I was/am involved in the development of a roughly 5 acre parcel on Kauai. 

I've been a part of some of these deal and the psychology of everyone involved is fascinating. 

I'm involved with buying the first rental property for our daughter.

Remember that title insurance involves multiple parties.

Most conventional wisdom/lessons learned are to the tune of not over leveraging, and any discussion involving >80% LTV seems to create a sense of nervousness (I am making a generalization here).

If you did, based on an appraisal or what valuation method?

I know you can gross more by using Air BNB, but how much more can you NET and how much more of your time is involved. 

Until we can get a down payment together I'm working toward getting my real estate license so I can get involved in the industry in my off time from the day job.