I set up the solo 401k and I am the admin and trustee.

Reason being, if you're shopping for a new PM, a nicer property with less of a hassle on maintenance will open that pool up.

I split my house up into three units.

You may want to consider tapping into a HELOC or an unsecured line of credit to finish this up.

There is not enough money in the associations reserves (built up over time from members monthly association dues)  to pay for the repair of three roofs.

I normally sign up for a year lease.

My loan officer is saying no, but the literature I'm seeing says up to 12 months delayed occupancy is allowed for special circumstances.

How are you going to make sure the contractors are showing up everyday.

When I look up this question on internet, it always says that in NYC, its the tenant who pays ...but in reality I am told that about half of Brooklyn listings are no fee (meaning that landlord pays) in order to get it rented fast.   

Are you meeting up with the guest before they enter the property?