A family member is going to be renting a room starting in 2018, what do I need to do in terms of paperwork/documentation, and how long do I need to rent it before I can show intent that it is an investment property?

We looked at a couple of flooded homes and the cheapest quote I received was for $58,000.

I've noticed a steady increase in the frequency of unsolicited mailers I receive offering my buy my house ("why worry about repairs, we'll buy you house as is, all cash, quick close" etc., etc.).

I would then have a lawyer draft a guaranteed maximum price (GMP) contract for your builder to sign with a very thorough scope of work and set of construction documents incorporated.

The fact that people will probably look up a business/investor on google even if they do receive the direct mail is a powerful observation.

You received good advice that while it is possible to go to the listing agent directly, I would not recommend it.

Since I’m not opening a LLC or anything like that it just goes on an additional document along with my individual tax forms.

It is the date of closing when the documents are signed. 

If I divide our "received at closing" money by 7 years I get 60+ K per year which is 100% per ...

Once you select one, speak with the loan officer and get him the documents he needs to do the pre-approval.