We ended up waiting him out, eventually he passed away and the municipality tore down the shack, obviously unpermitted shack and the gate. 

So you WILL cashflow eventually but go into the property expecting not to cashflow now.

Eventually, then turned to hiring it out to better use there time.

Eventually, you'll find someone who's willing to come down to your number.

No claim that this produces “the answer” — just a way to make tradeoffs explicit.I eventually put this into a spreadsheet so I could sanity-check my own intuition.

Eventually you may want property management. 

Those losses don't disappear — they carry forward and can be used when you eventually sell the property, when you generate passive income elsewhere, or if your situation changes (e.g., income drops below $100k, you qualify for REP status in a future year).

You'll eventually need the complete loan file, but those above would give me a way to know if we want to pursue the buy further.

@Naresh Yegireddi you also need to look into the locations of the building and general ability to re-tenant when then eventually leave or go dark. 

You mention managing the properties eventually.