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

If you are buying a house of any kind with mechanicals and roofs, you need reserves.

Was wondering other stuff like property management expense like getting a handyman to fix something or roof changes etc, assuming they are a bit more.

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.

It needed a new kitchen, new bathroom, new floors, a new porch roof, and needed to be totally rewired.   

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

If not, I suggest waiting until you do.If you use up all of your equity on your current home, rent it, and then need a new roof or boiler, your attempt at your first door will go sour.

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?

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.

Of those that require repairs, everything is covered by their deposit.