I have a machinist (past retirement age, but still working) who I trust like a brother.

You likely would not need to have it machined - unless it is gouged - but every time I take a head off, I take it to the machinist to check for warpage and and a valve test. I also get a pristine mating surface. It runs me $0-300.

you do not need to remove time-serts...unless they failed and pulled. This is unlikely. If they have failed, I will loan you my 1050 Big-Sert kit.

Here's a thought...Maybe you find a kid who is showing some automotive aptitude (maybe from a local vocational school?) and have him/her help you...It will make the job easier. I've brought a relative along in a similar manner, and he ended up doing an BMW engine swap on one car, and a manual swap on another before going to school for automotive engineering.

You should do this head gasket...This is no reason to get rid of it.