I was making $150k in my mid-20s selling insurance, bought the s2000, trips to Costa Rica and Greece, etc.

Expect this to cost a couple thousand at a minimum, probably wrapped up in the loan amount, with risk for an increased rate.When I started out people talked to me about refinancing like it was some magic bullet but if you're on an owner-occupant loan and refinance into a conventional/investment loan, there is a real chance your rate will go up substantially.

For example an A-class property is gonna cost a lot more and your ROR will be lower because of that but will appreciate better over time.

Now, I'm not saying a clever lawyer can't figure out how to make, argue and win a case like that, but I do know clever lawyers cost a lost of money and they typically don't work for free or only if they win in these cases.

My experience with property managers was that they cost a lot more than the monthly fee. 

You will be responsible for the inspection cost,  as the bank won't pay anything to fix anything.    

Per state law known as the “Costa-Hawkins Rental Housing Act,” local rent control can only apply to units built prior to 1995 (and in some instances earlier) and cannot apply to single family homes and condos.

Missing a key step or deadline will cost a lot more than the potential savings!

May cost a bit but I think it's worth it.

Normally, I give a warning when completing such things and let them know that all future actions will cost a fee.