@Ashley WishinskiI would have to say the only thing holding me back is lending, I am only 24(still building good credit) I don't have a normal job, I train horses and give lessons so I am  self employed, not something traditional lenders are to crazy about I have found out.

Can you somehow claim it as "self employed" instead of just capital gains to make it more official on paper? 

If the ladder, and you are self-employed consider opening a solo 401k before 12/31 of this year so that you can contribute as much as $53,000 and thus reduce your taxable income.

In order to make up for my military training/drills my employer allows me to participate with units on the base I am at, I also take my R&R's to conduct additional training with my unit.    

I don't have any income since I'm self-employed, and not paying myself anything, but I don't have any real debt either.

W-2 income is $113K and husband has self employed income for 2015 of roughly $20K, with an additional $50-75K expected to be earned by year end.

You do have to have self employment activity and no employees, however.

An EIN (tax ID) from the IRS is free and can be done directly on their website.https://www.irs.gov/Businesses/Small-Businesses-&-Self-Employed/Apply-for-an-Employer-Identification-Number-%28EIN%29-Online

No - life events are NOT (usually) necessary for roll-overs, but check your employer's plan's SPD (Summary Plan Description).You can keep the existing account open, and your employer (or you) can continue to contribute to it.

I’m self employed so I try to pay as low in taxes as possible.For additional income I recently started to house hack my primary home (4bed 2bath) I am currently house hacking renting 3 room each per month to international students for $650.