It is also important to note that some insurance agents are bound to certain higher levels of coverage than others.

That coverage will reimburse you a portion of your lost rent and legal expenses when a tenant defaults on the lease. 

Insurance is usually separated into two phases: 1) Emergency work (paid for by insurance which is partially covered by your deductible)  2) Repair Work (paid for by insurance depending on your coverage and quoted work)I would highly recommend a cashout... but chances are your premium will go up.

They may not even be willing to provide coverage to you at all as long as the dog is on the premise, or could jack up your rates significantly. 

I'd rather have $3m or $4m of umbrella coverage.

We’re looking for a software that will help us better organize our book keeping on the rental side but also on the construction side (we build rentals from the ground up so it’s almost like we have 2 businesses) We we’re looking at Buildium but we find it to be too expensive and comprehensive for our current size.

First your cash on cash return, next your overall cash flow, then your debt service coverage and finally your appreciation gain potential.

Andrew,Regardless of who you end up working with, pay attention to the amount of coverage on the 10 unit garage.

Flood Insurance Cost2. availability of property coverage based on proximity to the coast (windstorm exposure)Neither of those will prevent the deal but the costs of the insurance should be researched before you go forward so you can factor that in.There are now multiple private market Flood Insurance providers (Non-FEMA) and I would advise checking them as they can sometimes be significantly less.Contact a good Independent Insurance Agent with multiple markets and get some rough numbers for a sample property.

Generally, the coverage of the policy will state; “The coverage of this policy shall continue in force as of Date of Policy in favor of an Insured after acquisition of the Title by an Insured or after conveyance by an Insured, but only so long as the Insured retains an estate or interest in the Land, or holds an obligation secured by a purchase money Mortgage given by a purchaser from the Insured, or only so long as the Insured shall have liability by reason of warranties in any transfer or conveyance of the Title.”