welcome @Reed Tripp investor/reltor from Kitchener, but looking to partner up and leverage in the near future in the London/ St.Thomas area as well, it'd be great to meet like minded people near by, look forward to meeting soon

It would be the kind of discount you might expect from being on a busy street or near train tracks.

I haven’t spoken to lenders because I assumed since I didn’t have any sort of future investment to present to them, what is there I could talk to them about and what exact lenders I need to be speaking to. 3.

We expect you to be equally committed and, to that end, ask that you bring some money to the closing table.

My plan is to take the $800,000 equity I now have in my two unit building, wait until rates drop in the future and borrow against it to purchase a few other properties.

It just means your future deductions will be smaller.

I know they installed rear unit completely new roof in 2017, so the roof in front unit is the main concern for me that will need to be replacement in future, what I am thinking is that if I back out, I lose 11k, which the flat roof in front unit will cost less than 11k, I think you got great point here and I probably will stick with inspection in future, but mathematically speaking I was leaning towards account for roof replacement in future ?

The locations that haven't dealt with STRs can, and probably will, in the future.

If you're going in expecting to break even or cash flow, you're likely going to have an extremely difficult time.  

It's a way to show empathy while also setting clear expectations for how rent can be caught up.Look Into Rental Assistance: There might be some local government or nonprofit programs that can assist tenants in these scenarios.