If they break up in the future, I don't want to deal with who gets the place, etc.

I agree a decent landlord has not much at all to worry about in litigation.. most litigation comes from partnership breakups  construction defects and contract disputes. 

I have had many reach out who were just in a living situation they can't be in anymore (breakup, roommate leaves unexpectedly, transitioning to the area).

Break up with a girlfriend?

Hopefully soon that will break up some of the monopoly that Consolidated holds in the NEK and Stowe Cable olds in my neck of the woods and help the super rural folks who still have dial up!

Early move outs, break ups, domestic abuse, roaches, bed bugs, break ins, etc.

If you need to justify your purchases by having a discount on them - break up with your gf.

My best advice to you is to break up the home into sections, kitchen, bathroom, flooring, paint, framing, windows, doors, landscape, electrical (rough and finish), plumbing (rough and finish), etc.

You can break up the progress payments small enough to solve almost any cash flow issue for the contractor (I pay my drywall crew daily) but until the material is on the property and/or installation is occurring, there isn't a need to pay premature invoices let alone writing a 33% check weeks before a job starts.There are too many contractors that start asking for big deposits at the end of the month for me to feel comfortable prepaying for services in large amounts.