He only had a part time job, but his girl friend from Brazil, whose dad is a business tycoon will be paying the rent.

I travel with my primary job and a physician informed me about BP!

In regards to negotiating with the HOA that should be a No, I would assume if he owes $8k in back dues there's most likely a lien on the property if the HOA is doing there job correctly to insure they get paid.

After years of sticking with a job I hated and saving up enough money to feed my family for a little while, I decided to quit my "safe and stable" job to chase the dream!

Once you add those in you should probably be at a tax loss.

However, is on-site management more expensive than paying a realtor one month's rent and vacancy loss for about two months, per year?

I have excellent credit, a DTI of less than 25%, and a well paying job at a business I've been at for over 5 years.

I'd recommend as @Theo Hicks said to stick to a weekly report from your PM and then calls on as needed basis.Before you jump into this investment, ensure that the numbers work and the overall investment makes sense = low vacancy, demand is high, town population is on the rise, jobs are available and accessible, etc.Best of luck!

We both have good jobs and we're almost living on one income.

@Trung Le  We used the company which had done work in the house in the past because they had warranty for the job they did even though they are expensive.