I think you are de-sensitized to the hype of what is going on there, probably because you've lived there for so long. 

I’d love feedback; and I’m not sensitive, constructive criticism is absolutely welcome, I prefer straight forward answers, thank you all so much! 

I have been an IT consultant for many years and have happily taken people under my wing to teach them a skill set with no expectation of payment other than a cold beer or a celebratory lunch after they land their first contract.The 2nd question is a little more sensitive and ambiguous, but I am looking for average industry expectations for net income.

Maybe roommate 1 is over sensitive and not geared for renting a room.If you adequately screened roommate 2, I'd probably tell roommate 1 to get lost.

Obviously, there are risk and time sensitive considerations when employing leverage, but the return boost and the larger deals that you can access with bank money is undeniable.  

Because I am going to live there, I am location sensitive but high tolerance for "investing neighborhoods".

Most HELOC lenders only lend on primary residences.Additionally, as you're like aware of, VA appraisals have a heightened sensitivity for health and safety matters.

Sensitive nose buyers would never know it was a smoke house.

I suppose it's just a matter of keeping my ears and eyes open here and elsewhere to find the right team/pipeline including lenders who are willing to work with me.The good news is, If I cut my teeth in this environment, it should be really smooth sailing down the road.

I cut my teeth and built my fortune on the DC market.