I recently got into an accident with a driver that has no insurance, and I only have liability coverage.

Using very attainable #s, like projected rent, projected vacancy, etc. will go a long ways with insuring you make solid decisions.      

However, the lender for my refi  (who does a ton of investor loans) says purchasing this home (even with cash) puts my DTI over their threshold and jeopardizes my refi.I would still like to proceed with this second home, but how should I do so?

They also provide split roommate payments, screening, maintenance requests, applications, renters insurance, late payments, and expense tracking.

I am rounding to make it simplerGross income $158,000Expenses------------------Insurance        $11,500Office                $400Collections       $550Cable               $2870Property Tax   $7800Repairs/maint $12,800The expenses look a little low, but the owner is managing himself. 

How and with whom should we proceed with refinance options both commercial and personal loan routes?

Something else to keep in mind is a LLC does not provide absolute protection so you still need to take other measures to protect yourself like insurance, umbrella insurance policy, trusts to help further hide your identity, don't use your name and home address as the registered agent for the LLC. 

Does the transfer tax get taken out of our proceeds or do we have to come up the transfer tax upfront before closing.

The person who lives next door to me was listed in the paper this week to be in foreclosure proceedings.

I was told by a mortgage broker that because I own 2 homes CMHC won't insure my mortgage meaning I must put at least 20% down.Any ideas if this is correct or how I can get around this?