I've hired cleaners in house & covered for some local owners for a couple of months while they were out of town, and it's not very straightforward. 

They were charging another homes repairs to my home and wasn’t caught until I threatened legal action.I reached out to the new person who was managing my property to inquire about a lease renewal for my tenants and make it clear I needed to increase the rent to cover expense increases on the house.

I got caught in the storm last night but it looks like just off and on rain - should be OK most of the time and plenty of cover at the resort when the rain hits

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

I rent the second floor for 2100 which leaves me with the remainder payment of 1132.Am I generating cash flow since I have approximately 65% of my mortgage covered by the tenants?

It would cover them to move away until the unit is habitable.

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

They want to ensure that the property NOI is amply covering your debt service, and therefore able to cover the yield on the mortgage bond / MBS.As a quick example, let's assume that your property NOI fell significantly, because you decided to simultaneously renovate 25% of the units all at once (taking them offline, and causing NOI to sharply fall for 2-3 months).

If I hold title in the LLC they want to sell me yet another vacant land policy, but If I held title in my personal name my primary home owners/ umbrella would cover it.

We recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.