My goal is to supplement my main income with cashflow from properties but struggling to determine the best path to do this. 

Then it cut its dividend when the financial crisis hit and the company appears again to be in trouble as it finds its way in this new economy.I consider dividends from stocks to supplement whatever income I generate from investing in real estate.

- Supplemental income? 

They also want to get into REI as a retirement supplement vehicle, but are paralyzed by what seems to be a difficult situation to overcome, which is fully paying all debt down (Student Loans, C/C, Car Loans, etc.) before starting their investing.  

I will be retiring from my W2 job in a few years, so I thought this would be an opportune time to learn the business, prior to retirement, so that I have something to supplement my income.

I thought it was all BS, but a few years ago, a third school was built in my area to supplement the existing two and reported in the papers that schools in my area was overcrowded for years and kids had to be bused elsewhere.I know this home owner association president was also active in getting funding for a local playground that my daughter enjoyed when she was a toddler.

Ex: I want to supplement my retirement (30 years from now) with real estate providing 50-100k per year passively.

Secondarily, supporting charities and other organizations with time and expertise vs. just money.Short term REI goal: Purchase a STR along the Gulf Shores / Orange Beach area- Close to ageing relatives that will provide more opportunities to visit for direct and extended family- Utilize for family vacations over the coming years- Provide tax benefits to help offset W-2 income- Diversify portfolio that is heavy weighted towards mutual funds and company stockLong term REI goals:- Own 3-5 STR properties that can be utilized for different family vacations- Own MTRs/LTRs as opportunities arise- Provide supplemental income that my spouse could manage in the event of my death or disability (or less negatively, a career change)- Teach family (spouse and children) the benefits of real estate investing- Achieve financial independence with the goals to travel, enjoy activities, and devoting more time to "giving back"Questions I have:- With my stage in life, is it realistic to self-manage a STR properly?

Have the tenants supplement your residence while learning about managing properties is what house hacking is all about.Good luck

I will take all 3 in to consideration.My end end goal is to have a cash flow property to supplement my income.Honestly I would like to leave my current job and do something less stressful on body and mind.