Remember also that parking is a premium in the city.  

I understand what you are thinking in terms of self insuring to save the premiums and you will take care of any damages out of that account, however the bigger risk is the liability claims?

Call your insurance provider and give them the address for a premium quote.

Most property managers I have dealt with end up charging a premium for management of vacation rentals.

The cost of the acquisition plus the budgeted rehab costs are used to determine the premium.  

The primary factors that make up your premium are 1) reconstruction costs 2) fire rating 3) coverage levels on liability, separate structures and various endorsements and somewhere in there ( a black box so to speak) is your credit rating.

I'm sure the additional premium would be pretty insignificant to add 5-10K but if not needed why spend the money.  

Min. earned premium of $250.00, so set it up monthly and by the end of 2-4 months, it should have cost you the $250.00 that was the minimum. 

EARNED PREMIUM - PROPERTIES WITH UP TO 5 PHYSICAL DAMAGE LOSSES IN LAST 5 YEARS - CUSTOMERS WITH 1 LIABILITY LOSS IN THE LAST 3 YEARS- UMBRELLA POLICIES - TRAMPOLINES AND POOLS ARE THEY ALLOWED?

The reason you can not use a conventional financing is because you are considered to be a "Disqualified Person" to your IRA and are prohibited to provide a personal guarantee.There are only handful of lenders specializing in this type of financing and because it is a higher risk for the lender you normally will be required to put 30-50% down.Here is a list of such lenders that I've compiled over the years that our clients use, hopefully it will be helpful to you as well:https://www.biggerpockets.com/blogs/2810/50272-lis...There are also private lenders you can find locally (might be helpful depending on the property condition, LTV, speed, etc.) but expect to pay premium for those.