CMHC and the lender won’t give you the loan unless they perceive it as low risk.

Depends if you want the perceived federal stability.

This "re-training" has been addressed above as well but giving them the perceived control of depositing at an institution always seems to make them comfortable.

Having the letterhead will make your lease look more 'real' to help shoot down any perceived holes.  

I’m currently grappling with which path / options to take and would love all your thoughts – below I have outlined some context of my situation and options.Context:- Currently own 2 properties – my SFH (which I don’t want to move out of) and a condo that is rented (currently to family members which makes it easier)- Have 150k cash + 150k available from a HELOC at 3.75% -- have more available but this is all I want to allocate to REI right now (I say this so you know I’m not being super stretched investing the 300k)- I’m open to investing locally or remotely within the US – we live on the WC approx. 3hrs from SF- My wife and I work demanding 9-5 jobs – we are open and willing to spend material time on this but cannot make it our full-time roles for at least a couple more yearsOptions – I have outlined these in my perceived level of difficulty, would also love you thoughts on that 1.

If the IRS were to perceive that the risk of loss had passed from you to the buyer that would end your opportunity to do a 1031 exchange. 

If you think you found a needle in a haystack in terms of a great investment, I would hate for you to lose it over a perceived problem.  

They would have to figure out how to reconcile that to report a property that they havent been reporting.So basically there's a mis match between who the IRS perceives to be the tax payer for the property (you). 

Most contracts have an inspection contingency and you can walk away for ANYTHING on the inspection, real or perceived. 

But...rent is paid every month, on time, but usually sandwiched between complaints about other tenants, complaints about maintenance, etc.The problem is that they perceive their worth to you (and in general) way beyond what a reasonable person would.