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".

In cases where it's due to spousal abuse, she can get a restraining order, locking him out, but he still has to pay rent.As I said, I had plenty of cases where roommates move out, replacement roommates are found, the best course is to quickly vet them, usually, they are working people with a good history.

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.

If there's a hole, it may be a red flag.b) sensitivity analysis: I examine all the assumptions, and make sure I can live with the worst case scenarios.c) "Stall and see": if they are getting money over multiple years, and there is no penalty for investing later, I would usually wait so I get some real performance data, versus having to look at theoretical pro forma information.d) Recession stress test: I will not invest in anything, until I subject it to recession level stress and see if I can live with the result.

Sensitize that based on how much equity you will have after you pay down a certain amount of debt. 

This is probably more business focused because travelers are less price sensitive, stay for longer, and the travel patterns are more predictable.4.