Hello!

Does Urban Guide gives additional die to Will Test and Strength Test in combat in cities?

Does Urban Guide gives additional die to Acquire Assets Action in cities?

Does Leo ability gives additional die in wilderness combat (Will and Strengh)?

Is combat tests normal tests or special?

yes sure. he give you one more dice to any test in the city space. but not when you are in the other world encounter since when you in pass the gate you are not un city space anymore

Yes, Yes, and yes.

Notably Leo's ability should get an extra die when used in Wilderness spaces as well.

For location specific extra dice:

1) Is the investigator on the right location type (Cities for Urban Guide, Wilderness for Leo, Sea for Silas)? If so, then

2.) Are they conducting a test? Things like rolling a die to during a rest to see if a condition disappears isn't a test. A test is specifically when you roll a number of dice equal to your character traits like Strength, Will or Lore. Combat tests rely on these traits, so they are definitely tests. If so, then

3.) Is the type of test specifically enumerated or prohibited? The Urban Guide applies EXCEPT during Other World encounters, so you couldn't get their help to close a Gate. Likewise, while Jim Culver grants an additional die to Combat tests, he wouldn't give a bonus to Lore for the purposes of casting, oh say, Shriveling, because that's not a combat test. If the test is of a type specifically mentioned in the ability, OR isn't of a type specifically included, then you get the extra die.