One is a former primary (we refinanced once while still owner-occupied then transferred into an LLC when we moved out and began renting it, but didn’t have any issues with that one for about 5 years after we moved out).

You can take yourself out or severely set yourself back if things go awry.I've bounced around the investment mortgage industry for 5 years. 

I agree that Class C is definitely not the way to go unless you are just going to flip the properties to home buyers looking for a primary residence.

After a rough first year where I lost money for 8 months followed by another 4 months of learning how to self manage remotely, I had a great 13th-25th months where we have kept the placed booked, kept it profitable, and largely reinvested into the property.Here is the question though-  to buy the first property, my wife and I used a HELOC on our primary and used that for the downpayment on a new property,  for the furniture, appliances, etc, and all of the other little costs that go into getting going.  

One would be when you have a primary home and its listed on MLS (for sale) and the bank gives you the cash out until the home sells and the loan is set up for 12 to 18 months.

When I'm investing in trust deeds - my primary concern is the safety of the principal.

.• Primary residence: A 2-bed, 2.5-bath townhouse purchased in 2020 with a 2.75% interest rate.

This is where we will go back to your primary goal (Owning a cool property that you use sometimes vs. a pure investment property). 

MiThank you, I believe virtually all markets are over valued, but over the long term many (including my primary market) will have appreciation in excess of CPI. 

They must be claiming it to be a primary.