He was happy to allow me to rent out nightly because it actually helps keep his property in better shape than a long term renter (having a cleaner in there every turnover, short stay guests always let you know when something isn't working, etc) but didn't want to hassle with worrying about a percentage of income/management, etc.

Normally when a  property is advertised as "cash only" the property is in poor condition and/or the seller wants to reduce contingencies and opts for a cleaner transaction.

For example, my cleaner and handyman at my STR have separate cards so the only thing that ever gets charged to that card is that expense.

If it's a contact, then you can work with your cleaner to be that local contact.

Some properties there's just a Brita water pitcher the cleaners fill, others it could be bottled water cold in the fridge, and others would provide nothing because in all reality guests bring the drinks they want.

I recently paid someone to do my roof and replace the carpet (~5k expense) on my short term rental in 2023, however he won't fill out the 1099-NEC.

Not that I don’t enjoy dealing with tenants, maintenance, lawn care, Home Depot and Lowe’s trips and tenant change overs (I recently put new carpets, kitchen floor, appliances, vanity and mirror in the bathroom and fresh paint in my upstairs unit).

I remember visiting a buddy’s place in Austin years back..he had a similar setup over his detached garage and was convinced that adding a window unit and some carpet would let him count that space towards the home’s total square footage.

It was built in 2002, and I renovated the entire flooring by removing the original tile and putting Vinyl flooring in, there is no carpet within the house.

Inside mounts look cleaner and you can still add decorative window dressings.