Daryk, monbvol, that's all irrelevant.
We're talking about how you deal with a character role whose type or scale of activity is vastly different from the rest of the party. The issues - especially as they relate to character generation - are going to be similar no matter what the scope of the campaign is, or just how far out of scale the outlying character is.
Mobility: Battle Armor has very limited mobility, power and survivability, so their campaign goals and activities will be likewise limited. Adding an OmniMech to that mix gives them the ability to travel to places they couldn't otherwise reach (crossing obstacles greater than 90m wide or tall, evading forces faster than 30kph, defending the party against likely interceptors). In the context of players sitting at a table playing a game, the party is simply moving from one potential encounter area to another - just like a party of 'Mechs traveling by DropShip.
Rarity: DropShips are rare relative to small 'Mech units. 'Mechs are likewise rare relative to small infantry units. In terms of status and upwards social mobility, the jump from infantry to MechWarrior is way bigger than the jump from MechWarrior to Captain of a Leopard or Union. 'Mechs may be lost and replaced more easily than DropShips - but that's only a feature of campaigns focused on 'Mech-vs-'Mech combat, and doesn't hold true for campaigns centered on infantry squads, or on battles between flotillas of DropShips.
Monetary Value: Yes, you could trade a DropShip for many 'Mechs, enough to overwhelm a 'Mech party's expected opposition; but you can likewise trade an OmniMech for many battlesuits, enough to overwhelm a squad's expected opposition. Both exchanges have exactly the same effect on gameplay. Nothing you can do in character generation fixes that issue.
Losing the Tools of Your Trade: Exchanging the tools of your trade for cash should always,
always feel like a step backwards. You invest points in the asset and in the skills to use the asset, and that asset should be (over the long term, if not at every moment) more useful within the scope of the campaign than an equivalent amount of lesser goods.
Chargen Costs: Adding extra costs to being a DropShip captain is guaranteed to make that character less useful outside of their chosen role, but it does nothing to correct any of the problems raised. There's also the question of how many points a single character can invest in a single role before they become so useless (relative to the rest of the party) outside of that role that the party (or just the player) would be better off relegating that asset to an NPC.
Support Assets: This is decided during unit generation, not character generation. Not every DropShip has repair facilities (and none equal to a properly equipped repair yard). Not every DropShip has extra support staff for MechWarriors to borrow. Not every ship has enough organic security to secure the landing zone. Repair facilities, support staff, and security are frequently available without a DropShip being present - housed in groundside facilities, traveling in trucks, and so on. What assets are actually available to or commanded by the players is decided entirely by what kind of campaign the GM and players want to play.
I was looking at the benefits property give you, and noting that you could use the dropship as a form of justification for some of the property benefits.
That's fair. I like that.