Stop worrying about the boogie man and operate your business.Far too many landlords make decisions based on "what if" and only add unnecessary stress to what is not necessarily a stressful situation.Curb your imagination.

Study the fundamentals of a property in the market you are interested and as long as you are confident in your reasons, stick with it.If you are sure why would you be stressed out?

However, life is very comfortable and stress free debt free! 

But it is more stress since I am on the hook for the rent, utils, operating costs each month and I don't always breathe easy until I see enough bookings for that month to put me in the black.

At this point his voice sounds stressed and frustrated and he says that the offer is only open until Thursday 8/17.

I did a 1031 exchange a couple years ago... it was stressful...

September is next week - you should have tenants looking at it NOW.In conclusion, I can't stress enough how pictures are important.

With all the other things that can go wrong, I feel like owner-paid utilities are an unnecessary added stress. 

The tenant's girlfriend and the neighbor were in a hostile conflict and when the neighbor saw them moving in, the neighbor got really stressed.

If I had to start over and had 20k at my disposal I would:- Heavily research "wholesale" real estate and hire a reputable mentor- Follow that mentor's guidance and Invest in marketing after properly studying the business- Remain consistent and work HARD/SMART until your wholesale real estate business easily generates more income for you than your day job- Eventually quit your day job (after extensively learning the business and have savings stuffed away for 6-12 months)- Invest in properties with much more capital and knowledge than you currently have with a lot less stress and riskHope this helps!