This way, we continue to have cash flow coming in, and if we happen to have a bad contractor or one or two units and/or some permit/regulation related issues, the scale of the damage won't be too overwhelming. 

I'm a construction enthusiast and love everything about construction and learned how to build just by practicing on my own properties and pulling permits as an owner builder.

I'm a construction enthusiast and love everything about construction and learned how to build just by practicing on my own properties and pulling permits as an owner builder.

https://inewsource.org/2020/08/06/san-diego-overcharged-granny-flat-permits/ 

This is something that will come up when you permit anything through the city.You can add more than 4 bedrooms but depending on the area you will need to provide parking within the setbacks for each additional room.When you convert a garage you must have on site parking meaning it needs to be within the setbacks of the property. 

I love Comic Con and when I moved to San Diego for school I discovered it and its since brought me so much joy and this year was a bummer on that front.With regards to acquiring the property my knowledge is little to those here on the forum in terms of what makes something a deal.The input I do have is you may want to consider is that the garage conversion is permitted.

One thing we always do is make our purchase contracts contingent upon receiving an STR permit. 

Purchased a 3-2 single-family home with a permitted 2-1 ADU in Van Nuys, CA with conventional financing (20%) and added about $30k in repairs/upgrades/landscaping.

We have detailed plans from an online source, and we're looking for a GC or similar to help with permitting and building (water, power, sewage already here, but needs to be hooked up).This is fairly new to me, but would be finding a GC be the best first step, or should I reach out to the county with plans first?

Chances are you need a permit.