My head is all over the place and I would feel more comfortable doing this as a JV being that it will be my first.

The last tenants at one of my SFH rentals were comfortable securing the property remotely based on the photos and video tour, signed the lease electronically, and sent all move in funds to me electronically before they moved to the area.

Additionally, a property with a pool and a spacious backyard is a huge draw, as guests love the idea of relaxing by the pool and hanging out outside enjoying the fresh air.

Get out of your comfort zone.

For people that want more opportunity in their lives what comforts can they trade, what calculated risks can they take today for that opportunity/wealth in the future? 

I'm looking for advice on how to feel more comfortable pulling the trigger on my first out of state rental property.

One thing that would not surprise me is states setting up their own reinsurance programs for carriers and relaxing the risk retention limits.

Also, very important to consider whether your cleaning team is comfortable with maintaining the hot tub and balancing the PH between each guest.Our cleaning team empties, cleans and refills the water between each stay.

Another option is rental arbitrage, where someone trustworthy rents from you and handles it as an STR, paying you a fixed monthly rent.In the end, it depends on what you’re comfortable with and your financial goals.

This lack of sophistication with money leads many to avoid using credit at all and just continuing to operate within their comfort zone.