Based on my experience working with real estate investors and property managers, here are some common arrangements for local handymen and maintenance personnel for short-term rentals:On-call basis:Pay a set fee per call-out (e.g., $50-$100 per visit)Hourly rate for time spent on-site (typically $50-$100/hour)Additional charges for parts or materials usedRetainer agreement:Monthly flat fee (e.g., $200-$500) for basic availabilityAdditional charges for actual work performed beyond a set number of hours or visitsPer-task pricing:Agree on set prices for common tasks (e.g., $75 to unclog a drain, $50 to replace a lockbox)I like the per-task pricing as long as your maintenance calls aren't super frequent.I'm also a hard money lender if you're looking at a new deal to get quotes on soon or if you're looking to refinance a property soon!

However, he starts to talk about how you may sometimes overpay for a property because you are not necessarily worried about what the property is worth today but about the “long-term play.”

I've never stayed in a hotel or short term rental where I couldn't control the temperature.

@Rob WallaceCredit unions typically do not lend to LLC’s I will focus on another topic - I strongly recommend your operating agreement have terms preset if things personally go bad and one has to buy the other out.

They have been long-term tenants, and the prior landlord was apparently chasing the rent quite a bit. 

It's set to open in 2026 - I think that will be big for that area and short-term rentals.

Now both sides are long term rentals for me.

I am a beginner investor, I started off house hacking but due to my occupation I had to move and now that is being used as a long term rental.

Prepayment penalties- usually 1-5 year terms.

Those sales may happen off market between you two, or may have creative terms, but really you're negotiating two separate sale both of which only happen if you both like the terms.