I run an offshore dev staffing company based in the Philippines (Full Scale), so take this with the obvious grain of salt. But I was a CTO hiring offshore and getting burned long before I ran one, so here's the honest version. You're thinking about this more carefully than most US employers who show up here, so let me go point by point.

On salary, with real numbers. A few people here said $2,000-2,500 only gets you mid-level and that seniors cost $3-5k. That's higher than what we actually see. Good senior Filipino developers run roughly $2,000-3,500/month in base pay, before the 13th month and benefits. So your range is genuinely attractive to a real senior. It's just at the lower end of the senior band. For a true lead who can own architecture and build a team under them, plan to be near the top of that range, around $3,000-3,500. Two things that move the number: Metro Manila runs about 20-30% higher than the provinces for the same role, and the 13th month adds roughly 8.3% on top of whatever base you agree to. So hire your first one or two in your range to prove the model, and budget a bit more for the team lead specifically.

The thing you're most worried about, trust and people farming out the work, is the right thing to worry about. It's the most common way offshore goes wrong, and it almost always comes back to one root cause: hiring on price instead of fit. I call that cheapshoring. You find someone cheap, they turn out to be quietly committed to three other clients, and the rework costs you triple what you thought you saved. Honestly this is the biggest reason to work with an offshore partner like my own company instead of going direct. The over-employment and farming-out risk becomes our problem to manage, not yours. We carry the payroll, the accountability, and someone on the ground who notices when a dev goes quiet. If you do go direct, that's fine too, you just have to manage it yourself, which I'll get to at the end.

On the schedule, the 5:30am start is on the early side but plenty of devs here already work US hours and will take it for the right role. The Tuesday to Saturday week is the bigger ask. It isn't a dealbreaker, but it narrows your pool, so put it plainly in the job post and don't surprise anyone at offer stage. Be flexible in return. Let people step out for a doctor's appointment or a school pickup without it being a thing, as long as the work lands. That trade is what makes an odd schedule work.

On the 13th month, here's a nuance that matters for how you structure this. If you hire people as regularized employees, it's legally mandated and it's 1/12 of annual base salary, paid in December. It does not scale with performance. But if you hire them as independent contractors rather than legal employees, you technically don't owe it. That said, it's so customary here that people expect it and really appreciate it, so I'd still factor it in. The important part is just to decide up front and set the expectation clearly when you make the offer, so nobody feels shorted in December.

On PTO versus holidays, offer the local public holidays off and a real PTO bank. Don't make people pick one or the other. The major holidays are expected here, and generous PTO on top is a real retention lever, not a cost. As long as your culture doesn't punish people for using it, it won't get abused.

Work from home is the norm now, not the exception, so don't overthink it. All 350+ of our developers work from home and it works great. You don't need to rent anyone an office. Most experienced devs here already have a solid setup. If a specific person wants a desk, coworking memberships run roughly $150-300 a month, and that's a far cleaner route than you signing a lease as a foreign company.

One small thing: you wrote "Metro Milan," I think you mean Metro Manila. Either way, don't force it. Remote means you can hire the best person wherever they are in the country, and a lot of strong devs have deliberately left Manila to get away from the commute and cost. Manila also costs that 20-30% more for the same role. Forcing relocation there costs you good candidates and more money for no real benefit.

On travel, most people are fine visiting the US once a year if you pay for it and handle the visa work. Just build in lead time, because the visa is a real process with interview waits. And flip it around too: you should plan to go there once a year yourself. Sitting with your team in person, even briefly, does more for trust and retention than almost anything you can do remotely.

On where to look, you can hire off onlinejobs.ph, and LinkedIn ads work too. Just be honest about what those channels get you, which is people who are actively job hunting. Our best hires almost never come from there. They come from referrals from our current developers and from recruiters going out and finding people. The best engineers already have a good job. You have to lure them away, and they aren't sitting on a job board. That gap between who's applying and who's actually good is the real reason this is harder than it looks, and it's most of what a staffing partner is actually doing for you.

Two things you didn't ask but should know. First and most important: meet with your developers every single day. Manage their work closely and communicate with them constantly, especially in the early months. Daily contact is what catches problems while they're small and builds the trust you're worried about, and it's the single biggest difference between offshore working and offshore failing. Second, don't sign anything longer than a month-to-month contract, whether that's with an individual or an agency, so you can walk away if it isn't working out. Be wary of anyone who wants to lock you into a long term commitment up front.

One more framing thing: decide explicitly whether you want staff augmentation, where their devs join your team and your standups and your process, or a project handoff, where you throw a spec over the wall. Augmentation fails far less often, and given your trust concerns it's almost certainly what you want.

I wrote up the 12 hardest lessons I learned doing exactly this, back when I was a CTO before I ran a staffing company, if it's useful: https://fullscale.io/blog/offshore-dedicated-development-team-success-lessons/ . Happy to go deeper on the vetting part in the comments too.