Hey Amanda, If these are residential properties, then you have 2 options for refinancing - 1) Conventional - Takes your income + debt and thats how you qualify. 2) DSCR: Takes the monthly rent - payment and thats how you qualify, pretty simple.If these are commercial, then you will have different options as it depends on the type of asset they are and cashflow. 

Ideally using STR AirDnA projections as well.

Happy to point you in the right direction, I've worked with different types of lenders and you just have to find someone that understands your scenario.

From what I see in your post, the only issue thus far is expecting 20% down on an undesirable collateral type to most lenders...Cheers!

I don’t know what to look up or what to type when it comes to understanding how each city is doing when it comes to RE and/or what to look for. 

Everything is highly individualistic and there isn’t a “right or wrong”, but what works best for you and your situation. 1) what is your ultimate goal for your ideal investment property?

Ideally you want to be all in (purchase + renovation budget) for less than 80% of the after renovated value of the property.

What made you interested in investing in this type of deal?

Home warranties are a type of insurance basically.

Unless you are rather experienced with this type of damage, it may be hard for you to tell the extent of damage.