Clay Tile to Flat Roof Interface

I have a home built in the 1920’s. A portion is steeply pitched with clay tile. The remaining is a flat roof with tar and gravel. I need to re-roof the tar and gravel and would like to put a membrane roof on that part and refresh the felt on the tile portion (I don’t know how old it is but it has the original tiles). There is a chimney in the interface between the tile and flat roof protruding into the tile section. All along the interface, I from time to time, have some water leakage into the house. Minimal which I’ve been able to patch with tar so far. Several questions:

Can I interface a tile roof to a membrane roof? If so, how is this best done?

I’ve yet to find a contractor who does tile & membrane. It does not seem reasonable to do this in two pieces. Suggestions?

The house is located in Albuquerque, New Mexico.

Should not be a problem if you have a good roofer.

Run the membrane three± feet up the steep under the tile. Run the membrane around the chimney as sub flashing and finish(counter flash) with copper or lead.

link to more pics

Do not settle for a contractor who can do the membrane well but has no clue on the tile. Find one who can do both well, or have one who does membrane well and one who does tile well and have them work one after the other. With input from both.

Any roofing contractor worth his salt will do both app’s for you, especially down there where tile is prolific.

Nice work Dennis.