If you talk with insurance companies they may bring your insurance cost down if you do certain things like put in flood vents at lower elevations.

Arrive early, have your elevator pitch ready to introduce yourself.

If you do build a second story generally better to have an elevator especially medical office so consumers that are older in age can use it. 

@Evan Crawford - your friend could try to get a surveyor to perform an elevation report.

2) Should I declare income that I receive from renting a bedroom on my taxes to help elevate my income levels?

No elevator but it is only one flight

I don't think you need to cut them out of your life, but as you progress through your goals you will find like minded people that will elevate you to the next level and that is who you want to surround yourself with.

There are a lot of factors that go into the cost of flood insurance... even how much the house is elevated off the ground can save hundreds.

I worked in corporate sales for 25 years and sold elevators for 17 years for the same company.

One thing to remember is humidity and lack of hiking w/elevation.