-Place-
Cherrygrove City (Johto)

-Type-
Fire

-Pokemon-
Cyndaquil (0-4)
Quilava (5-13)
Typhlosion (14-18)
Houndour (3-9)
Houndoom (16-18)
Slugma (0-4)
Magcargo (12-18)
Numel (1-9)
Camerupt (10-15)
Lampent (10-15)
Chandelure (16-18)
Litleo (5-13)
Pyroar (14-16)

-Stipulations-
I would look for adaptability and creativity.
Adaptability: Using offensive maneuvers defensively to prevent damage. Using defensive maneuvers offensively to counter/damage me.
Creativity: Using maneuvers to accomplish something other than it's intended purpose.
From 0-4 Badges, I wouldn't have any limitations or stipulations. Just a normal "defeat my Pokemon with all of your Pokemon."
From 5 Badges and on, a challenger would only be able to use as many Pokemon as I would use.
From 10 Badges and on, a challenger would only be able to use as many Pokemon as I would use. The challenger would be able to choose the Pokemon, specifically, but the order in which they are used will be randomly determined.
From 16 Badges and on, a challenger would only be able to use as many Pokemon as I would use. The challenger would be able to choose the Pokemon, specifically, but the order in which they are used will be determined by me. Switching Pokemon, from both sides, will not be allowed unless the Pokemon is determined to be defeated, otherwise, the round is considered forfeit.

Map of Hoenn (clean)
Map of Hoenn (routes/cities/landmarks)

Map Proposal, created by rolling dice to randomize. Every distance started with Long (80km/50 miles), Standard (30km/20 miles) or Short (15km/10 miles), then I rolled a certain number of d6s and flipped a coin to determine whether those d6s are adding or subtracting kms.

For example, for the short route between Littleroot and Oldale I rolled 1d6 (6 on the die, coin flip decided subtraction, so the final distance between Littleroot and Oldale is only 9km). For standard routes, like Route 117 between Verdanturf and Mauville, I rolled 2d6 (10 on the dice, coin flip was positive, so the final distance is 40km). For long routes, such as Route 110, I rolled 4d6 (110: 11 on the dice, subtraction, so the final distance is 69km).

Finally, the routes and non-route areas all have a certain level of travel difficulty, each of which interacts with foot, bike and surf travel. Standard travel times are:
~4km/hour or 32km for a day on foot
~15km/hour or 120km for a day of Acro biking or surfing
~20km/hour or 160km for a day of Mach biking
~100-200km/hour in flight, depending on the speed of the flying Pokemon used as a mount. Travel difficulties do not generally affect flight.

Level 1 - Smooth, unobstructed flat terrain or equivalent (e.g. the Cycling Path between Slateport and Mauville). This level allows 50% faster travel by foot, surfing and Acro bike and 100% faster travel by Mach bike.

Level 2 - Mostly smooth terrain, with some obstructions such as rocks, trees and/or mild elevation shifts (e.g. Route 117 between Verdanturf and Mauville). This level allows 25% faster travel by foot, surfing and Acro bike and 50% faster travel by Mach bike.

Level 3 - The "standard" route difficulty, with a mostly coherent path, but multiple obstructions, significant elevation shifts, large numbers of wild Pokemon and other slowing factors (e.g. Route 113 between Route 111 and Fallarbor). This level balances all of the various means of travel to the standard numbers mentioned above.

Level 4 - A difficult route, with rough terrain, dangerous weather, strong currents/choppy waters, severe elevation shifts, and/or highly aggressive Pokemon (e.g. Route 119 between Route 118 and Fortree). It's easier to get lost on such a route. This level causes 25% slower travel by Acro bike and surfing and 50% slower travel by foot and Mach bike.

Level 5 - The most dangerous of routes, with incredibly inclement weather, powerful currents, strong and aggressive wild Pokemon and/or little to no defined path (e.g. the Great Hoenn Desert or Routes 132-134 between Pacifidlog and Slateport). This level causes 50% slower travel by Acro bike and surfing and 100% slower travel by foot and Mach bike.

I've just included the most basic of notes on the routes and cities.

Areas, Seas and Routes (Town/Town, Town/Route, Route/Route)

The South-Western Area of the landmass is dominated by Petalburg City and otherwise heavily forested. Oldale, an outlying town, is a common place for advanced Pokemon trainers to practice battling, in the shadow of prestigious Johnson Academy. The further suburb of Littleroot is barely a town, just Professor Fir's research laboratory and a few outlying houses. Oldale connects by river and land to the southern end of the Cycling Road and Route 110. The southern half of Route 104 is the site of Briney Marina and its beaches, and ends at Petalburg Woods, a dense outcrop of forest that forms a boundary between sleepy south-west Hoenn and the well-developed Rustboro Metropolitan Area.

- Route 101 (Littleroot/Oldale) | Short land, Lv. 2: 9km
- Route 102 (Oldale/Petalburg) | Short land, Lv. 2: 17km
- Route 103 (Oldale/Route 110) | Standard land/river, Lv. 3: 38km
- Route 104 South (Petalburg/Petalburg Woods) | Standard land/coast, Lv. 2: 40km

The South-Western Sea is a lengthy series of routes connecting first Briney Marina and Petalburg to the island town of Dewford, then connecting Dewford to Slateport. Many commercial and ocean science ventures are based out of Slateport, making it one of the most important cities of the region.

- Route 105 (Petalburg/Route 106) | Long sea, Lv. 2: 68km
- Route 106 (Route 105/Dewford) | Short sea, Lv. 2: 19km
- Route 107 (Dewford/Route 108) | Standard sea, Lv. 2: 37km
- Route 108 (Route 107/Route 109) | Standard sea, Lv. 3: 24km
- Route 109 (Route 108/Slateport) | Long sea/coast, Lv. 2: 99km

The Central Area of the landmass is dominated by the massive technological marvel that is Mauville City, the center of the region in more ways than one. As they say, "all roads lead to Mauville", and it has major land routes in all directions, connecting Rustboro in the west to Slateport in the south and Lilycove in the east.

- Route 110 and Cycling Path (Slateport/Mauville) | Long land, Lv. 3 and Lv. 1 respectively: 69km
- Route 111 South (Mauville/Route 112 and Great Hoenn Desert) | Standard land, Lv. 3: 21km
- Route 118 (Mauville/Route 119 and Route 123) | Short coast/sea, Lv 2.: 13km

The North-Western Area of the landmass is dominated by Mt. Chimney, and all of its geographical features stem from the volcano (except for Meteor Falls). There are a few mountain and foothill towns, most notably Lavaridge and Fallarbor, and a large number of difficult-to-traverse routes, especially around the mountain (see the Jagged Pass, the Fiery Path, the Great Hoenn Desert and Route 115).

- Route 112 (Route 111 South and Great Hoenn Desert/Fiery Path and Lavaridge) | Standard land, Lv. 4: 39km

The Western Area of the landmass, or the Rustboro Metropolitan Area is the center of government and commerce in the region, with both the Hoenn Rangers and the Fairfax Association based there. Rustboro is connected to the rest of the region through Rusturf Tunnel at the end of Route 116.

- Route 104 North (Petalburg Woods/Rustboro) | Standard land, Lv. 1: 24km
- Route 117 (Verdanturf/Mauville) | Standard land, Lv. 2: 40km

The Northern Area of the landmass, or the Fortree Jungle, is wet, with near-constant rain and very heavy plant growth. Much of Route 119 from Mauville to Fortree is overgrown and difficult to traverse, making it a common route to fly over rather than brave on foot. Once past Fortree, the going is somewhat easier, and there is more development as you move towards Mt. Pyre and Lilycove.

- Route 119 (Route 118/Fortree) | Long land, Lv. 4: 92km
- Route 120 (Fortree/Route 121) | Standard land, Lv. 3: 40km

The North-Eastern Area of the landmass has a massive bay containing Lilycove Harbor to the east and in the center, venerable Mt. Pyre. Lilycove is the major national harbor of Hoenn, and receives visiting ships from such far-flung places as Kalos and Unova on a regular basis. This has turned it into something of a tourist destination, especially considering its massive Megamall, the Hoenn Art Institute and Mt. Pyre.

- Route 121 (Route 120/Lilycove) | Long land, Lv. 3: 68km
- Route 122 (Route 121/Mt. Pyre and Route 123) | Short sea, Lv. 2: 21km
- Route 123 (Route 122/Route 118 towards Mauville) | Long land, Lv. 3: 64km

The North-Eastern Sea is a dense archipelago of inhabited and uninhabited islands, with Mossdeep and the Mossdeep Space Center as its main notable features.

- Route 124 (Lilycove/Mossdeep or Sootopolis) | Long sea, Lv. 3: 71km
- Route 127 North (Mossdeep to Route 126) | Standard sea, Lv. 4: 25km

The Eastern Sea is very natural and relatively undeveloped, lending it a mysterious air. The great crater of Sootopolis and the dangers of Victory Road are whispered about on the mainland, but rarely visited, only seen from afar.

The Southern Sea and its only city, the floating metropolis of Pacficidlog is paradoxically both well-inhabited and completely inhospitable. The currents, jetties and weather patterns are unpredictable and dangerous, braved by only the boldest of ships.

Non-route Areas (Caves, Forests/Jungles, Open Ocean, Mountains, Desert)

Minor Settlements (Villages, Camps, Outposts)
- To be added as they become important