Although cash flowing properties are pretty much impossible, we love the neighborhood and our families are near by.

This does not sould like an impossible situation to work through.  

In real practice that is something that is impossible to do profitably and efficiently. 

Not sure how the market is where you are but here it is competitive but its not impossible.

When I was presented with a prospect that had a service/support animal, I informed them that the property itself was not ADA compliant and any accommodations for a physical disability were financially impossible to perform due to the number of stairs. 

I've done that multiple times for various subscriptions that had some asinine cancellation term buried in their 6pt font 20 page terms and conditions, and for companies that made cancelling impossible because of a lack of responsiveness.

So if you transfer a property to an LLC, you either need the bank's approval in advance or you need to refi at that time, and refi'ing with a new LLC can sometimes be challenging, even if it is cash flowing (not impossible though).There are also some legal concerns.

Also buying properties out of state (and country) isn't impossible but can be a bit difficult as well.

It would be impossible for me to in all good consciousness raise it $300, I just can't, I would rather give up on it. 

Its not impossible, but I bet for every 1 MoCo wholesale deal I see, I see 30 for DC and 30 for PG, and maybe 5 in Virginia.