@Delaney Best No problem, welcome to the forums! 

It’s best to consult with your attorney and tax professional to figure out what works best for your situation.Usually, there are NO tax savings with both.

The two primary banks I worked with no longer exist  and all of my original banking relationships have moved onto different banks/lending institutions.

. - No one is building office of any sort right now, and net new supply will be low for some time. - Prices reflect this pain in office- Many high income earning millennials are, finally, moving to the suburbs.

I have no need for the rent collection or tenant screening as this is a function my property manager does for me. 

If you continue to house hack, I see no reason why you should sell the property.If you did a 1031 exchange, are you able to cashflow greater and/or target a better an area with higher appreciation rates? 

We're hoping to appeal to the military population, but as you said Kevin, no luck so far. 

One is a condo with a mortgage left of 320k @ 4%, is capable of being Section 8 @ ~$3.8k per month in DC (no rehab necessary).Next two are houses that are completely paid for.  

We have done nearly a decade of actual conversion analysis, and that is the reason no one figured lead generation out and why so many simply do it wrong.Drop these "companies" and focus on generating your own leads through SEO. 

I have the reserves in place for the 5% down payment, 15K for emergencies, and have no debts!