I can tell by now if someone is BS'ing me or if this is just a temporary situation.

I read somewhere, I think on this site, that an ESA letter must be signed by a mental health professional practicing in the state where the rental property is located.  Now I can't find anything about it.  I have also...

With both strategies you need to find the right opportunities.In my opinion if you're buying a $2 million plus beach property you're probably buying based on emotion and not based on numbers.  

After the first one, I'd advise to be more analytical than emotional, but do what you love, leave yourself some cash cushion, and jump!

Is there a disadvantage to using Roth IRA as a temporary holding place and wouldn't it be a wasted opportunity to hold in my checking account where it will not grow?

Im just concerned with our temporary income level. 

There are many aspiring investors who become overly emotional when they first hear the success stories of those who have been able to scale quickly and eventually replace their income.

I've also seen pieces of luan used where siding was missing as a temporary fix.http://www.gaf-weatherside.com/

I have deep emotional ties to this home.

Allowing a problem to persist is not the lesson you want to teach your sons and that’s far more important than the temporary discomfort of addressing the problem head-on.