While an investment like this may pay off really well in the future, it may also kill your investing career before you make it out of the nest.

Not really using leverage; I'm okay with small potatoes based on my age, nest egg, and risk/reward profile.

It doesn't sound like you have much of a nest egg, no land lording experience while needing to borrow lots of money to purchase numerous properties that will provide minimal if any positive cash flow. 

I'm interested in self-directing my Roth IRA and investing in real estate.I recently read Tax-Free Wealth by Tom Wheelwright and he stresses the point that you should not nest a tax-advantaged investment in another tax shelter.

Your nest egg is great, credit score is great, self-employment is not so good.  

Protecting your nest egg seems to be more of an uphill battle than even acquiring those funds in the first place.Temptations with shiny objects always seem to get me in trouble at least. 

I know nest is good. 

I am assuming this can be dangerous if they are building nests or anything or biting electrical wires.

From a liability standpoint you would want the property nested in an LLC.

And I want to do this in 5 years or less.How would you manage to take my $300k nest egg and do what I want with it?