These will eat away at any "cashflow" you may have.2.Tenant Issues: Properties in certain areas may face challenges with tenant behavior, making it tough to maintain the house long-term.

For higher-end properties in Cincinnati, everyone seems to claim they can handle it, but then there are performance issues. 

Given that affordable housing is a national issue it seems that the more pathways to home ownership is a good thing.

Circuit Court of Appeals late Thursday reinstated a nationwide injunction that had been issued earlier this month by a federal judge in Texas who had ruled that the Corporate Transparency Act was unconstitutional, Reuters reported on Friday, thus suspending the deadline once again for most reporting companies to file beneficial ownership information (BOI) reports with the Financial Crimes Enforcement Network (FinCEN)."

https://ecode360.com/15245641#15245642 seems like condo conversions is not permitted in Hoboken but curious what's the result of your case. 

Has anyone ever had a similar issue to this?

In my state the standard contract used by realtors addresses this issue by allowing the agent to check a box specifically to limit the seller to keeping the EMD as opposed to going after "liquidated damages" like that.

I keep a very healthy amount of reserves to avoid using my insurance unless I have a catastrophic issue.

Other than cost overruns and unforeseen issues, I think it's just a question of if this is worth it.

From simple rules like permits to outright bans so that is a huge risk IMHO.