On the other hand everyone has to start somewhere, so how much confidence do you have? 

I appreciate the confidence boost @Bruce Woodruff!

Following David Green's Core 4 strategy (realtor, contractor, property manager, and lender) gives confidence to invest anywhere.

Thats what I did in 2019 and it gave me much needed confidence to grow my portfolio. 

Are very confident it will be covered 3. the amount paid out will be worth it. 

So I’m fairly confident they were not trespassers. 

Start with low-commitment options like REITs, gradually exploring bigger deals as you gain confidence and market knowledge.

Once you have this team in place, you should have the foundation to invest in any market confidently while not being there physically.https://www.biggerpockets.com/blog/core-four-real-estate-team

I personally don't know the investor very well, but I have a close friend that has lent money to him on multiple occasions within the past six months, which gives me a little bit more confidence. 

I'm pretty confident there are other solutions out there for the property.