@Michelle Eisenberg - Congrats on your decision to invest in real estate! 

I’m not sure if it’s the best decision or not, but I’m more looking to validate the thought process and get feedback.

What I don't get is that people, after reading less than 10,000 words on a person's 96 year-long life, somehow glean enough information to questions her decisions and throw around phrases like "more like a hoarder of money than an investor and I am not impressed" and "total lack of caring for family".No talk about her work ethic, loyalty, selflessness, wiliness to learn, discipline?

These would be finding people who haven't listed their property but likely just need the easy button and a nudge from you to make their decision to sell.Moving outside the city to some surrounding counties can help as well.2 good targets for you to Consider: Absentee Owners with Equity and Seniors with 15+ year ownership.Here are some suggestions for your area counties,Absentee Owners: 13,256 Home value up to $300,000, single and multifamily, high equity Adams 1970   Douglas 122 Arapahoe 1162   Jefferson 1703 Boulder 863   Larimer 2643 Broomfield  49   Weld 2737 Denver 2007    Senior Homeowners: 9881 availableOwner Occupied, age 60-89, single family homes, High equity, home value up to $350,000, 15+ year Ownership AND Low Financial Stability Scores (FSS) Adams 2710   Douglas 38 Arapahoe 1211   Jefferson 771 Boulder 343   Larimer 523 Broomfield  29   Weld 1205 Denver 3051

I'm not familiar with IL agents, but I know most around here have you sign something saying not to solely rely on the agent's advice when making an investment decision. 

She is beyond help being this far behind and making such poor choices for so many months.

Secondly, many condo associations are run poorly and have little in the way of financial reserves, so unexpected repairs, maintenance, or upgrades could translate into surprise special assessments that will gobble up your profits.Flipping off-market properties is a sound strategy, but it requires serious marketing effort.

Make sure you keep emotion out of the decision.  

When I made a decision to help others, I realized people wanted more doing than reading and quick answers to their questions.

So far, it's been a good decision in that I've been able to learn landlord basics, how to do a cosmetic rehab, and live extremely cheaply.