My agents comps showed the home being 260k-300k, and they were confident rent could be over 2400.

(I am not confident when it comes to future-telling thus this is just my naïve prediction)I am happy to help anyone who is interested in learning further about my experience with the company, you can message me.

Once the word gets out that this place is available we have confidence we will get the guests to stay. 

In fact I have less confidence that a random property manager will fill my property with a good tenant than me doing so myself. 

I'm fairly new to investing and, whereas several CPAs have talked a decent game, I've struggled to find one that makes me confident they know this world. 

@Ed Ma, I want to second @Nathan Gesner's advice here -- perhaps only sell if you are relatively confident in your landing spot being an improvement for you. 

BP has some great pod casts that helped me gain confidence when getting started but also help me now by keeping me up to date on current topics. 

@Amanda Scheller Since you are able to house hack with as little as 3.5% to 5% down one suggestion would be to buy your first place in San Diego and hold on to the 4plex....If after your first purchase you feel good/confident about going to the next purchase, at that point you can consider selling the 4plex to purchase your second property in San Diego.  

Feel free to revisit any sections where you feel less confident.

If you are going for more appreciation (and it is in an appreciating market) the taking a lower cash flow might be fine.If you're confident with your rent number and the fixed expenses you have, then the only thing to negotiate is price and terms.