Phil T wrote:
Welcome Jack.

Recessed transom washers are a sign the nuts were overtightened. This is a frequent and common item. No need for concern.

Answer 1- The item to look for is excess sealant around the washer on the inside of the transom and between the engine mounting bracket on the outside of the transom. if excess sealant is found, it is indicative of proper sealant. if there is no sealant, you could remove on bolt at a time, add sealant in both locations and reassemble. Note - see item below on engine height.

Answer 2: Only BPR (Evinrude) included a bracket that was designed for trailering. All other brands have a bracket that allows the engine to be locked in the fully tilted up positon to allow it to be serviced.

While there are dozens of "transom savers" that connect the engine to the trailer, most recommend products that support the engine to the transom. See these products:
https://m-ywedge.com/
https://www.simyamaha.com/accessories...-supports/
https://www.wholesalemarine.com/t-h-m...r-support/

I trailered two of my boats for over 10 years, thousands of miles without an issue. My current boat, trailered, I use a modified 2"x4" with rope ends tied to the transom lifting rings. Last year I did Whaler Gatherings in MI, NC and VA without issue.

* Engine Height - If your engine is mounted with one empty hole above the top set of engine bolts, consider raising the motor 1 additional hole. This will give you better performance. Not a day 1 item, more of an off season thing.