They are the perfect example of working hard all their lives, saving what they could, and hoping what they saved will carry them through (philosophy of the 'poor dad' if you will).I have a few thoughts, but this is a savvy, intelligent forum of investors with a variety of specialty areas so I would love to hear some creative ideas of how they could generate some additional income throughout their retirement years. 

I see that you already own international real estate properties but not generating income from them.

Are you looking for long term generational wealth or just some side cash to supplement your current salary?

I'd lean more towards random bonuses throughout the year rather than having them come to expect it every quarter.My handyman charges a visit fee of $40.

I’m generating a list to market to and would like some insight on what would be the best strategy to use as far as direct mail, or any other tactics that can get a better response rate. 

Generating Leads:First, things first: (1) there are opportunities available on the market, (2) you do not need to become best friends with a real estate agent BUT you do need to have your stuff together; before you call the agent, make sure you have your financing in place & that you have figured out how much cash you will need to make the purchase.

My plan is to move out shortly and start generating cash flow but am concerned what heating costs will be like with the renters able to control the thermostat and not being as diligent about keeping windows and doors closed.

@Jonathan McDermott not necessarily, it would depend on how much interest and dividends you're generating and being paid.  

In my opinion, You’d be much better off, much better bang for your buck and you’ll likely spend less capital up front If you house hack here than buying an investment out of state in a random market.

I’m getting into real estate investing to be able to provide for my family and build my way to generational wealth.