They may be doing us a favor. 4 people have already told us that 135K for this home is overprice in its current condition.

I’m wanting to put in more offers to have numbers in my favor, but I’m looking for the line not to cross if there is one.

If you get that right, the future should always work in your favor. 

Based on my perspective and walk through, I have determined a tear down is most likely the more favorable approach rather than repairing each defect one by one.

Since he's stayed in the property for about 6 months and Baltimore has very favorable tenant protection laws, I'm sure he has some sort of right to stay, legally speaking.Does anyone have any advice for how to handle this?

College kids favor texting over email so I would include that method of contact as well. 

Consider firms that have a very favorable split and don't charge you if you don't close a deal every 3 months like some do.

Quinones-Sanchez is actually rather developer friendly (Clarke is not), this may be a balancing act for her constituents since she has been able to pass some investor favored overlays recently. 

You can always do a cash out refi- I recommend waiting 6 months so you can get the most favorable terms, but you can still do it. 

I've also entertained the idea (as a way to compromise with my dad) off starting of with a wholesale deal and using that profit to finance a rental property or two and sort of perpetuate that strategy to get exposure to both avenues which may consequently lead to our continuing this strategy or choosing one of the two that  we may favor more than the other.