The Big Items
Housing is the primary battlefield, and the "Rent vs. Buy" equation is currently rigged against both sides. If you are renting, the numbers provided are $1287 for a one-bedroom and $1493 for a two-bedroom. Let's be realistic: these are baseline figures. In the "nicer" corridors like the ViBe District or near the oceanfront, you are looking at $1700+ for a one-bedroom without much effort. The trap here for renters is the lack of rent control and the sheer volume of transient military personnel, which keeps vacancy rates low and landlord leverage high. You are fighting for inventory against a guaranteed paycheck (military housing allowances), which keeps the floor artificially high.
Buying isn't necessarily the wealth-building play it used to be, either. While the median home price data is missing here, the local reality is that the median sale price hovers around $380,000 - $400,000. The trap for buyers is the "Flood Factor." You can find a house that looks affordable, but if it sits in a flood zone (and a massive chunk of the city does), your mortgage payment becomes a three-headed monster: Principal, Interest, and Escrow. That escrow includes homeowners insurance and flood insurance. Furthermore, Virginia is not a low-tax state for property. You are looking at a property tax rate that averages around $0.99 per $100 of assessed value. On a $400,000 home, that is $3,960 a year just for the privilege of owning the dirt, and that number will rise as assessments chase the hot market.
Taxes are the silent killer of your disposable income. Virginia has a progressive income tax, but don't let that fool you; it hits the middle class hard. The rate jumps from 2% to 5.75% relatively quickly. If you are making that $50,127 target, you are losing roughly $2,500 - $3,000 of that gross income to the state before you even see it. Then there is the sales tax. The combined state and local rate in Virginia Beach is 6%. It sounds standard until you realize that services, repairs, and dining out all take a hit. There is no "break" for the working class here; you pay the same rate on a gallon of milk as a millionaire does on a steak dinner, which is a regressive kick in the teeth.
Groceries and gas show some variance, but don't expect a bargain. The US baseline for a single person's groceries is roughly $300 - $400 per month. In Virginia Beach, you are looking at $350 - $450. Why? Logistics. While the port of Norfolk helps, the city is an island-adjacent peninsula. Fresh produce and goods have to cross the water bridges, and that cost is baked into the shelf price. Gas is similar. You are usually paying $0.10 - $0.20 above the national average due to the coastal location and specific Virginia fuel taxes. The local variance is stark; a gas station three miles inland is often $0.15 cheaper than one near the oceanfront tourist strip. If you aren't hunting for deals, you are lighting money on fire.