When the borrower is also my contractor, does the lien waiver schedule change?

The lien waiver question is actually the smaller issue here. Let me work through both.

On the lien waivers for your cabin build: the fact that you're his lender on a separate deal does not change the mechanics of how you collect lien waivers from subs working on your property. You get conditional waivers at each draw, unconditional waivers on final payment, same as any construction job. A sub filing a mechanics lien against your cabin is filing against your property, not his. Your position as note holder on his deal sits in a completely separate collateral stack. Those two liens are on two different properties and do not interact the way you're describing.

The conflict you're actually describing is not a lien priority question. It is a structural one. You will be in a position where your GC's financial distress, if it happens, damages you twice simultaneously. If he runs into trouble mid-project on his flip, the same cash pressure that threatens your note repayment could cause him to slow-walk or abandon your cabin build. You would be trying to call a default or negotiate a workout with someone who is also holding your permits and relationships with your subs. That is the risk your question did not name.

The LTV here is $110k against $165k ARV, which is roughly 66.7 percent. That is workable as a hard money position, but the assumption doing the most work is the ARV. If his ARV is based on comps from a hotter period and the local market has softened, that cushion compresses fast. Confirm how he's arriving at $165k and whether that's a formal appraisal or his own estimate.

On the conflict question specifically, an attorney needs to tell you whether your jurisdiction imposes any disclosure obligations when the same person is simultaneously your borrower and your contractor. That is a one-question call, not a lengthy engagement, and it is the right question to bring him.

What is the source of the $165k ARV, and have you seen his draw schedule for the funded project?

The dual-role risk is real but the lien waiver mechanics on your cabin don't change because you're his lender on a separate parcel.

The thing I keep circling back to is whether your lien position on his property and your payment obligations on your cabin are actually as separate as they look on paper. If he's GC on your cabin and a sub there files a mechanic's lien because he didn't pay them, that lien lands on your cabin, not his. That's annoying but manageable. The weirder scenario is the reverse: if he defaults on your note and you move to foreclose, any outstanding sub invoices on your cabin that he hasn't closed out yet could become leverage for those subs to slow things down or complicate your draws. The real question I'd want answered before March is whether your state requires the GC to provide conditional lien waivers from subs before you release each draw, because if it does and he controls both the invoicing and the waiver collection, you've handed one person a lot of rope.