Otherwise, sounds like you've covered all the major considerations, other than the biggest one - if that's the route you want to go. :) 

Those who are in the business of collecting debts on others’ behalf are covered, but original creditors are not.

Taking it a step further, I thought it would be a good idea to consider multifamily properties where I could rent out the other unit(s) to cover the mortgage (or even better produce positive cash flow) while reserving one unit for my vacation home. 

You wouldn't want to forgo 9% in returns to get 3% or negative returns in real estate.Also, if you have gains, you would need to not only make at least 9%, you would also have to earn enough to cover the tax and fee consequences of cashing out your stocks. 

Thanks for the suggestions, I would have to reread the lease again to be sure, but I think it says something like the tenant is responsible for the first $100 of a repair and then we would step in to help cover the cost if it’s more than that. 

A "true" umbrella policy covers everything that you own, so companies want to have all of the underlying policies in order to maintain positive control over liability and policy forms. 

Sounds like you guys are doing it right covering a lot of avenues.

The loan was going to cover purchase and rehab.

Hello,I am looking for a landlord policy that covers replacement cost on the roof?

This will cover a insurance increase as well as compensate you for this risk of having the dog as a tenant.