I have a very good friend who is also a loan officer, so leaning on him for financing advice and best practice has been invaluable.While I can overcome the first widely conceived barrier to entry (money), I find myself hesitating to pull the trigger.

No matter what reason you list, the tenant will resent it and it's conceivable they will damage the property and be uncooperative. 

@Navtej Singh Saini great saying:  "what the mind of man can conceive and believe, it can achieve!"

But conceivably yes. 

This is a federal law (an ill-conceived poorly written one, but the law of the land nonetheless): https://vimeo.com/407748080

If you're living in it and trying to rent it before you move out it would be hard to argue that it is an investment property - especially because it is probably not being treated as an investment property on your tax return.But if you moved out and converted it to investment and have tried to rent it and your intent was to hold then it could conceivably be considered being held for investment. 

@Akash Amin it’s conceivable you could get a bank to accept a subordinated loan as a partial downpayment, keeping your own contribution at 5%, if they keep their own loans.

I want 10k a month in rental income by the time I'm 45, so if I have 20 doors with $500 cash flow per month, then conceivably I've done that.

It was itemized for everything conceivable that could need to be repaired.

You are writing a contract on a house and conceivably you should have a way to close if you can't assign it.