For the masses, taking out debt on liabilities is a sure way to force your way into a bad situation.

The barrier to entry is higher, the rate of debt is higher and in my view, the liability will get linearly higher too.

It shouldn't be an issue to put title on both properties, unless you want to maximize liability protection and create another LLC

Now a landlord (and architect), I wouldn't build out the space without the second stair since it really is a safety issue/liability (especially in case of a fire) if anything were to happen.Full excerpt of building code below:According to the Chicago building code on egress requirements, the third story above grade plane within a dwelling unit [which in this case is the duplex-up unit], all the following conditions must be met:1.) the building is equipped throughout with an automatic sprinkler system2.) the floor area of the story does not exceed 1600 sq ft3.) the dwelling unit has an exit that discharges directly to the exterior at the level of exit discharge.Your third story attic space is unlikely to exceed 1600 sq ft, but you'll probably find the sprinkler system to be cost-prohibitive.

Before I purchase an insurance policy I wanted to seek some guidance on the best way to proceed.I received 1 quote so far for a HO3 policy that has 600k+ of dwelling coverage, 70k of additional structure, 450k personal property, 200k loss of use, 500k liability, and a few extras like equipment breakdown, water backup, service line.

The property manager doesn't come on site because they say its a liability.

Hello,I was recently told that if I or my partner personally complete work on one of our flips that we own under and LLC that it voids the liability coverage within the LLC and we as individuals would open ourselves up to Liability.

If you want your LLC to be respected for liability purposes, it should have an operating agreement, bank account (so an EIN) (this will also require disclosures to the bank on your identity), and for you to full respect it as a separate entity from yourself. 

The borrower has already shown the ability to repay and since you did not originate the loan then you are not on the hook for liability.

If you could bring your own work in to an appraisal office, you would be an asset to them, more than a liability.* Along the previous line - research specific lenders and find those that do "direct engagement."