Ensure your agreement has no pre-payment penalty.In my experience, private money loans (which is what this is, as also previously explained in prior responses) typically come at a higher rate ~ 8%-12%.  

They specialize in short-term rentals and have a local presence, which is a big plus for ensuring guests have a seamless experience.3.

I want to ensure that I understand the closing documents.Thanks in advance. 

Do you have any go-to strategies for ensuring everything comes together?

This gives him a chunk of money upfront to do with as he sees fit, ensures he gets steady income (with interest), and reduces his tax burden.

Make sure to dive deep with your lender on the analysis to ensure you make the right decision based on goals, short and long term. 

With an attorney handling the eviction, you can not only ensure proper handling but also take advantage settlement agreements to prevent having to restart the process if the tenant were to default again and get automatic final judgment when the tenant defaults on the settlement agreement. 

They will ensure everything is square.

.#2 Repair Management, tracking expenses, following up with outstanding work orders, ensuring work completed with photos by vendors, notifying owners when there is a repair request by the tenant and track the time it takes from work order to completion, track the amount of repairs to a home at end of year so owner can see those expenses and try to get them on service contracts and off home warranties.

Whatver you decide, you'll want to ensure the proper addendum is attached to the lease to specifically outline how utilities are handled and charged if charging tenants.