Personally I have never been a fan of pre-tax accounts (401Ks and IRAs) because I feel like they constrain my ability to invest in the assets I want, so another consideration you may have is to temporarily stop those investments to save faster for your house.

I’ve been reading about DSCR for a few days now and this has been at the forefront of my considerations for what we’d like to do.

That is a major consideration. 

Considering you purchased in June and with the drastic increase in rates over the last month, everyone we are working with we are recommending to line up the refinancing: get through processing and underwriting, but don't "pull the trigger" on it until rates soften. 

Anacostia, while considerably better than it use to be is no where near class B.

Can Only a PART of paid OPTION Consideration Funds be NON Taxable ?

I’m looking to become an investor in the KC area and I was curious if I should pull the trigger on a multi family or single family home with the VA loan?

That is a great list of considerations for what most investors are looking for.  

The tradeoff on the joint financing is going to be the (refi) costs associated w any transfer of ownership, HOWEVER transferring title to the LLC is unlikely to trigger due on sale (b/c it sounds like most banks simply aren't monitoring and/or enforcing due on sale in these instances) which would make the ownership (sans the actual mortgage note) more easily transferable than exiting your position as an individual owner?

I most want to avoid spending considerable time showing units in-person to prospective renters, esp. before we've pre-screened them.