I already have an umbrella policy so not sure if upping that premium or moving it into any sort of trust/land trust or something else would be a smart move. 

If indeed it was the properties spoken of as 50% then Bill's suggestion will solve that as well as making sure that the surviving person is the beneficiary of the insurance policy along with a power of attorney for the business affairs in the case of death or other incopasitating injury.

The last line in there pisses me off because I see it made in so many public policy arguments.

I know each lender might have different policies surrounding this, I just want to get an idea of what is the normal practice.

Insurance can remain seperate on one property or you can use a blanket policy, won't usually matter.These are not usually long term financing arrangements or fully amortized depending on the loan amount.

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Title companies vary on there policy.

Net rental income for the new one will be (75%*rent) - PITI.

In your case, the absolute best you can do is to pay your PITI payment and the PM fee (typically 10% of collected rent.)

@Brad Zerhusen My closing costs were:$206 Filing Fees$7,100 Origination Fee$3,500 Appraisal$16.00 Flood Certificate$1,810.32 Title Policy$2,537.40 Lenders Attorney Fee's$7,100 Mortgage Broker Fee's$10,428 Tax Escrow$10,036.74 InsuranceAnd I received $15,374.66 for tax proration.