The exception to having to be able to cover both property's expenses would be if you can document the rental income of your first property - which would necessitate you moving out of it first and having it rented.  

I haven't had the best luck with it, but probably didn't give it the attention it necessitated. 

But, if ever questioned, you just need to be able to explain/document the “unexpected” situation that necessitated the move.  

It also has a floor issue that necessitates it being replaced.

The words "at my discretion" necessitate the contingency.

Don,t sweat it,checks and balance,dishonest people have necessitated changes in the process.Full speed ahead...................

Taking advantage of the frequent military necessitated moves.

NYC may still be in contention, but possible not.If you are looking to buy a place to live and your job necessitates being in Toronto, then sadly you are in for big prices ... even with a commute.If you are able to invest elsewhere in Canada or the USA, you will get more returns for your money ... more in the US than here at home.

Personally, at this stage of my life, I choose to work from home, travel a lot with the family when I can, and leave the on-site micro-management of properties to others (so that I can be free to "chase the next deal" online from wherever I may roam - which leads me to invest in condos (essentially hassle-surprise-free), setup online infrastructures for management (managing teams via emails and telephone as opposed to managing properties hands-on), and aim for a multitude of "spreadsheet" properties as opposed to two or three "big money making" ones, which would necessitate personal attention in most cases.

Syndication is an advanced technique that necessitates a track record.