I now have 13 and figure I need 50 to replace my job.I'm cautious by nature so I haven't been as aggressive as I could have been but I'm getting more so.

@Lelith WalkerYour governing documents should outline the procedures (judicial foreclosure, non-judicial foreclosure, etc.) the state of New York may also have provisions in their condominium law that governs how you can collect.

I have three comparables on the same street of the same historic nature (much higher value too) and other figures in the industry agree with my comparables including the cooperating agent.

First of all,  Security deposits  as rent should ONLY occur on the last month, and never before then - - otherwise you have nothing to hold over for damages on move out.QB is poor when managing security deposits, and when I asked this on a QB forum, you should have seen the procedural mess that was suggested to make it all work. 

Thanks for breaking the procedure down in simple and relatable terms

It's worked out great as I've done a few large apt deals and my experiences and earning potential is far greater than I ever thought was possible this early on.I say this because its natural to want the safety net from leaving one good paying job and wanting to jump back into someone else paying you for another job.  

@Jd Martin bad income is very subjective and there's always a chance that I excel in the field because I have a natural business mindset.

Typically this is the responder, someone who is in a tight spot and might overlook the impersonal and unprofessional nature of the YL.  

My primary concern is the changing nature of renting a unit in a building whose units are being converted to day rentals, comparable to Airbnb.

Naturally, I'm Canadian, so I need someone who understands both Canadian and US tax laws.Ideally, if they were located in Markham or Richmond Hill, it would make it even better!