Quote from @V.G Jason: Quote from @Carlos Ptriawan: Quote from @V.G Jason: For folks saying their bookings are already up or well reserved for 2023, what % of cancellations did you guys see in 2022 once it came to fruition?

You will also want to confirm the loan and asset values minimus.

My dilemma is this: I would ideally like to wait until I have emergency cash reserves to cover 6 months of mortgage payments for all 3 properties.

It doesn't sounds like you have enough equity to do much since you would need reserves for two properties then.

I would reserve appraisal gaps for hot markets, but I suspect the appraisal will come in at the price offered.  

I have confirmed using this lookup tool: (https://myhome.freddiemac.com/resources/loanlookup) that my property is owned by Freddie Mac (Results of query >> Yes.

We are sitting at about 60% LTV on it and it cash flows very slightly with the current rent, reserves, etc. but it has that pool, which is not ideal on the expense side.

Your tenant has already signed the new lease, which confirms his agreement to the new rent amount, sending that notice via certified mail can act as an extra layer of documentation that can be helpful in maintaining clear records. 

It still cash flows after paying all bills and reserves.

If you are concerned about doing things perfectly legal just find a lawyer that can help you confirm it, and restructure if needed.