This is a very labor intensive process for most big box skip trace companies because it cannot be automated.

On an ADU the process can take a year from start to income.  

I created the following decision tree diagram to illustrate the decision process (click to enlarge).The above decision process is based on the property’s performance record, with the goal of achieving financial freedom in mind.Financial freedom is not just replacing your current income.

I wanted to refi but I am unsure of the 1. the process 2. is it the best call?

Quote from @Emmanuel Rugamba: Hi everyone I am 26 year old professional athlete looking to buy his first home but also house hack in the process.

Having to use their lender is annoying, but for someone who has done it before or at least knows it can be a frustrating process, it's worth it for the deal they give you. 

However, weigh the costs of selling and the potential long-term appreciation you’d lose in this area.Real estate investing is a learning process, and you’re already ahead by taking action.

Or is it better to go directly to the city to get the permit process?

Had clients use them, and they claimed the process was way too tough of pulling funds. 

Aside from that, once I was to get it under contract for assignment, just looking for any potential roadblocks or anything like that just in case while I proceed with the process.