Like maybe I could pull enough out from heloc on primary residence to pay off debt and then rent out my primary and use the extra cash to payoff heloc and then do another heloc once the original one is paid off.

I'm considering converting the shed into a DADU to maximize the use of the space and earn some extra income. 

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

It shows you are serious and willing to go the extra miles to make it work.

Insurance is expensive, there is a lot of extra maintenance like painting or electric in common areas that don't apply as much with smaller units. 

Finally, of the extra $200k, how much are you putting into operating reserves? 

Unfortunately they don't care how much your worth they care how much you earn a month.

It 12 years, assuming you make no extra payments, you'll have a paid off condo that cash flows a lot better. 

Partnerships are earned through trust first especially when you are ready to put any sort of money down. 

(I’m ignoring any extra cap-x because you said it was a condo, but you’d also add any major cap-x to cost basis).