If you consistently analyze properties, it will be much easier to recognize a good deal when it shows up.

If you consistently analyze properties, it will be much easier to recognize a good deal when it shows up.

We also have to recognize that younger generations are looking for more flexible living arrangements.

In searching existing STRs, it is very clear this happens in practice, but I am not willing to buy a property and gamble that we can do an STR.

If you "wait" for a down market,1) you will not know when the market is actually "down".2) by the time you recognize it, it will be too late.3) you won't have the resources, skill, knowledge, or involvement in the market to make a play.

Unfortunately LLCs are not recognized as a flow through entity in Canada, so you cannot apply the foreign tax credit on your personal taxes. 

Not likely but it’s a gamble versus a scalable business approach.Develop an operating agreement.  

I decided to gamble on appreciation and overbid on a duplex that will have good cash flow in Oak Park after losing another all cash deal (I bid all cash, over asking and was outbid by a buyer with similar terms with an offer “well above” mine on a different property in the same neighborhood. 

If you consistently analyze properties, it will be much easier to recognize a good deal when it shows up.

We tried to put it on the Facebook marketplace, but the address is so new that Facebook does not recognize the address and will not allow us to proceed.