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.

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

I wish y'all the best and look forward to my real estate journey.Keep Elevating,Woodly

People seem to forget that as an owner you ARE the HOA, and I don't think most people realize that a good HO6 policy has coverage against special assessments.I will also chime in that an older well managed building (preferably without elevators) can be a much lower cost risk than many of the larger newer complexes in Denver many of which have had litigation against their builders already, and whose taxes are often double or triple.  

So, how does one find an investor without time to do the "elevator talk"?