I was looking to have fun and live (rent) near downtown or the domain but maybe the more logical and financial idea to buy a place and then rent out.

After several visits, I've narrowed my search to areas near(ish) to downtown (Roosevelt, Coronado, and Encanto) that I foresee transplants from CA being drawn. 

I agree that option 1, really is a dangerous option and only makes sense if you currently own NOTHING and are buying a multifamily to house hack and live rent free.Option #2 I would absolutely AGREE is a ton of work and also IF YOU ARE DEDICATED to being an investor, is the best option.

And if you dont own your primary property then take the loan and buy yourself 3 to 4 family in the other borough with FHA loan(3.5% down) and live rent free and make little extra cash flow. 

My wife and I live in Winston Salem—she’s a born and raised and I’m a transplant from NY.

As for what I mean by where we want to live, really 2 things.

I would start planning on how to house hack and live rent free in college.

I would rather make a few visits over a short period of time to get my house back now than to have a tenant game the system and live rent free until the courts open up for these types of cases...currently October but might be delayed. 

LL are more likely to sell when they have to go through the hassle of an eviction and have the unfortunate event of having someone live rent free in their unit for up to a few months.Unemployment in San Diego is significantly higher than the national average (estimated at over 30% in San Diego, nationally the rate is ~15% - So our unemployment rate is near double the national average) and higher than during the Great depression (it is at an all time high). 

Doing this gives you experience in managing tenants, it gives you "street cred," and it gives you a place to live - rent free … if the numbers work.As to choosing whether to do a flip or not, consider your personal position on the matter.