Is your assessment $355,000 or your implied market value $355?

Your goal should be to find a happy medium where you enjoy the lifestyle of the place you live and are comfortable investing where it makes sense.And the answer to your actual implied question is "Yes!".

Those guys that said THEY gotten bids accepted at 44% implying that they have some special sauce are something else.  

If you are changing careers and your income will go down significantly (you said change, I implied decreasing), why not keep the money as a back up/emergency fund in case you need it?

This implies that the city cannot demand the removal of an unpermitted issue and any red tag on an unpermitted unit unrelated to safety you have 5 years to address.  

If by "residential loan package" you are implying a "Mixed Use DSCR Loan" unfortunately doesn't sound like it would work since the commercial unit is larger than the residential

If / when it becomes common for sellers to not pay then buyers will be bent over the barrel and I foresee more lawsuits regarding representation or implied agency ahead.  

This implies that min/max state setback, size, parking regulations are the regulation to apply in the case of local regulations (city, county, HOA) are more restrictive. 

An advertisement that markets a contractual position to acquire real property from a person with either equitable or legal title and does not imply, suggest, or purport to sell, advertise, or market the underlying real property is permissible under this section.People need to read closer.

Will absolutely push the due diligence time in order to make the decision and if the seller is unwilling given the circumstances, i think as you implied that is perhaps a bigger red flag than anything!