My biggest question is this: do you think I should continue to rent for now and prioritize tackling loans?

I think hard money lender to take this risk cannot legally charge appropriately which means the law is working against you (the law meant to protect owner occupied owners from unfair loans).I agree with @Jay Hinrichs that your best option likely is to sell on the mls.  

I think I am just south of you? 

And you are thinking of trusting someone who will also make money off this transaction ?  

Regarding borrow's DTI, Chase thinks that this item is not that important.I wonder will my high DTI impact the loan underwriting?

5unit is probably manageable.  20 unit is work I would think. 

I'm building some currently (so obviously I think that works). 

However, I don't think I will be able to borrow against it due to the fact that I have already gutted it. 

You know this and the reason I am saying that I am considering in getting a real state license is the connections, the access to listing off market and possibility of earning commission that I can use to increase my portfolio.I think that being an investor agent will help me build a reputation and that can be good or bad.

I didn't see anywhere that you posted what they said ARV was, or what you think it is based on comps...the County assessment has no bearing whatsoever on value.