We recently had that balcony completely resurfaced, so we shouldn’t be having any slope / waterproofing issues from the deck of that balcony. - We’ve also inspected the roof / parapet wall, but don’t think those are the culprit because the issue presents itself on the 2nd story, not the 3rd story that’s immediately below the roof. - Plumbing issues have been ruled out.

Sounds overly complicated with little-to-no benefit.

Justin,It sounds like you are considering adding the queen to the loft area, along with the sleeper sofa remaining. 

.- The MTR strategy is great and you have the advantage of listing it with multiple different platforms.  3/2 will attract a certain type of of MTR client, one that travels with families most likley or displaced families, so your pool of applicants may be a little limited- If the long term play is appreciation, than breaking even sounds good.

The cost of constructing a replacement house is completely irrelevant.

That sounds like a great partnership.

Your landlord sounds like a flake, a self-managing hobby landlord who hasn't realized he shouldn't be self-managing if he can't shut his stupid hole when the chips are down and not make empty threats.

Does that sound like a good strategy? 

Hey @Sofia Sharkey, sounds like @Justin Morgan has got the low down on the area!

Insurances, contractors, realtors, off market properties, cold calling, etc all seemed so difficult....BUT...After 1 year, I've now completed multiple rehabs, have more properties in the pipeline, have investors on board, and all of those worries are now just day to day operations.