No deal will ever feel perfect—it’s easy to overthink, but the best way to learn is by diving in and taking that first step!

I have never purchased anything 'perfect' but all of my rentals could have been rented as they were upon purchasing them. 

We have a few markets we target outside of California, but obviously if you want to stay close to home, Sacramento would be an ideal choice.

I really want to start my investment journey but I'm not sure if an out of state property would be a good choice while renting in NYC or if we don't move, to move to a cheap market, live in the property for a bit and then rent it out.

So give those folks the choice...go pick veggies or lose your welfare payment.

I would suggest buying without value add only if you were going to keep the property at least 10 years. https://www.neighborhoodscout.com/ca/san-diego/real-estateI think your plan to rent in San Diego is likely the correct choice especially as you get to know the area. 

I believe we are making the right choice by doing legal/fully permitted ADU's.

Some will criticize your choices, but understand that their judgment often reflects their own insecurities.

You will never have perfect knowledge.

Landlord had to move to a different state to have better access to healthcare, i.e. did not move by choice per se.