Hello!

I'm taking a stab at this just to figure it out, as it's not the same as the 4th edition rules I'm use to working with.

Laughing Vulture, the T-Bird pilot lives in a cascade mountains smuggler camp and spends most of his money keeping his V-TOL working.

Let's start with squatter, as he basically lives in an old campground that's now a semi-illicit smuggler town for the Cascade Orks.

SQUATTER
See category description on p. 373, SR5.
Comforts & Necessities: 1[2] (4S)
Security: 1[2]
Neighborhood: 1[2]
Points: 2/2 [4]
Cost: 500 a month

As you can see, there are three areas that can be improved, and 2 points to spend, but spending those points on ratings will increase the base price by 10% each point spent. Those points are also used to buy special features for the dwelling, but those features have prices all. Essentially, the points work as a cap on how much customization you can do, and you get more options at higher base lifestyles. If your base lifestyle is high enough to meet the "minimum" rating for the feature, taking it just costs points, but doesn't include the price increase. There are also lifestyle options that modify the entire lifestyle and tend to give or take points or alter the caps or base values.

First up, Laughing Vulture lives in the cascades, so let's apply an appropriate Lifestyle Option: W Zone, which makes it clear he lives out in the woods. Here's what it looks like now:
Comforts & Necessities: 0[2] (6s)
Security: 1[2]
Neighborhood: 1[2]
Points: 3/3 [4]
W-Zone: +1d6 hours to response time
Cost: 500 a month

He's going to need a place to land his aircraft, but he doesn't really work on it himself (he's got a mechanic contact that does that) so I don't need invest in the Garage (Aircraft) option, let alone the shop/facility that goes with it to make is functional, which he doesn't really have the skills for anyway. Instead, we'll just get him a lot to land it in.

Comforts & Necessities: 0[2] (6s)
Security: 1[2]
Neighborhood: 1[2]
Points: 1/3 [4]
W-Zone: +1d6 hours to response time
Yard
Cost: 550 a month

Next, he's a rigger, so having a reasonable quality matrix connection is important to keeping him functional. The Public Grid has a -2 penalty to all his remote-drone action, so getting a better Grid is a priority here.

Comforts & Necessities: 0[2] (6s)
Security: 1[2]
Neighborhood: 1[2]
Points: 0/3 [4]
W-Zone: +1d6 hours to response time
Yard
Grid Subscription
Cost: 600 a month

Ok, now that base fatigue damage value is 6s, which is a bit annoying. I'd like to get Comforts and Necessities up a bit to reduce that. Laughing Vulture lives way out in the mountains, which means he's more than just in a W-Zone, so I can add the Obscure/Difficult to Find option too (which has modified rules from the base rule book.) This option boost his lifestyle points to 4, twice the starting rate for a Squatter lifestyle, which is the cap. However, I think the nature of being in a cascade ork smuggler camp might improve he security a bit, so I can still pick up Extra Secure for the lifestyle because it doesn't involve lifestyle points.

Comforts & Necessities: 1[2] (4s)
Security: 1[2]
Neighborhood: 1[2]
Points: 0/4 [4]
W-Zone: +1d6 hours to response time
Obscure/Difficult to Find: -2 to sneak up to/observe, no deliveries.
Extra Secure: D-zone for security response.
Yard
Grid Subscription
Cost: 750 a month

This means he lives not just out in the woods, but in an obscure place out in the woods that is otherwise an E-zone. The response time for security is 1d6x12 minutes +1d6 hours, which I guess is how long it would take to get some official tribal security forces to bother responding to a Cascade Ork smuggler camp. His personal security setup has a dice pool of 2, which means he probably keeps most of his valuables in his VTOL because the shipping crate he calls a home has a cheap lock. It's more secure than a tent, but not by much. It's not a pleasant life, with the plumbing being an old camp shower shared with some others squatting in the old camp ground, and the heating being a camp fire which also doubles as his only cooking option. He needs to resist 4S fatigue damage from the environment just from staying there, but being an Ork he can probable survive that. He has grid access to entertain himself, but he probably needs to use his RCC's signal boosting abilities to get a connection from home.

It's probably not the smartest build ever, but it really fits my concept.