There is one currently in place but I feel is pretty weak needs updated.

I always labeled those who couldn't commit to something 24/7 or those who "stopped to smell the roses" as weak or unmotivated.

I've inherited a few rentals with chronic late payers.

He does live in Toronto...Even so, I have a hard time imagining how a weak US economy (Greg S's prediction) could be good for Canada or Canadian investing in the US.As for the original question, Trump is unpredictable and never detailed his plans, but a republican senate, house and president should be good for RE investors as it relates to RE policies (tax codes, 1031 exchange, new policies, etc.).

A weakness of earning interest income from hard money is you have to pay a lot of tax on it if the money is not in a retirement account.  

The next tenant you get simply  avoid forming a emotional attachment to and strictly inforce all rules, if you choose, without having the weakness of your emotions interfering with your business.

My RE weakness is costs associated with rehabbing, and just wanted to verify my numbers are in the range of what folks have already done.

However, the pool of buyers for those markets are relatively weak compared to ours for good reason.

Once you have examined your strengths, weakness, and desires pick one area to try at first. 

@Jaysen Medhurst mentioned the risk of an assessment and I also don't like an HOA telling me what I can or can't do with my property.The weakness I see in your plan is moving to NYC.