However, if you don't have "earned income" (as opposed to capital gains) then you cannot contribute to a Traditional IRA or HSA and deduct it from your taxable income.

He’s been earning on it for 10 years and maybe he thinks he still can, but there was already a serious water damage issue due to the property sitting 10 feet below street level and water building up every time it rains.

Do you want the cash flow or do you need some extra cash right now?

As out of state investors, my partner and I have extra costs that local investors don't always have to account for (IE: local can self-managing, access a local handyman, leverage existing relationships, etc.).

For smaller properties, an extra vacancy can throw the property immediately into negative financial performance. 

You marry for money, you earn it.

There are certainly many advantages for investing in your own backyard in terms of existing relationships, understanding the market and extra peace of mind especially when just starting out. 

That being said, I will definitely be reaching out to pick your brain and see what I can do for you to earn your time and experience.  

I also agree with some of the posters above that you want just go ahead and factor in property management into your numbers when looking at cash flow (even if you just use that extra 10% to pay down principle or reinvest).

I’d like to be earning 10k a month in no more than a years time.