Salem

I used my free teleport to go to my friends place, after that, i made a leanto there and can teleport to boston and leanto back and forth. Then, I looked at the wilderness guide and he said I will lose my homestead if I choose to do the random teleportation (and I cannot do the friend teleport anymore). So, if I do the random teleportation will my leanto teleport function be disabled? will I be able to teleport to friends place ever again?

The new lean-to becomes your homestead. You'll still be able to travel freely between your homestead and Boston (or other major city on the server), but you'll not be able to go back to where you were via teleports. You'll have to use the old fashioned mode and walk.