Real estate pricing is based on demand and desirability so very cheap properties are often money pits with high maintenance and high vacancy.

Advani underscores the use of modern software solutions for everything from rent collection to maintenance requests, suggesting that technology is not just an option but a necessity for contemporary property management.He also touches on the importance of building a community among tenants, whether through events or shared spaces, to boost retention rates and create a more desirable property.The Future of Construction: Innovation and SustainabilityIn the construction segment of his discourse, Advani delves into how technological advancements and sustainability are becoming increasingly pivotal.

My true goal is to earn enough cash flow to 1) cover my necessities and general living expenses and 2) replace my W2 (I have the approximate numbers for these goals based on my own personal ambitions.)Based on your comment, it sounds like I should strive to own high quality real estate in medium-high barrier to entry (read desirable, appreciating, etc.) neighborhoods.

Also a desire to be a landlord and be willing to do landlord type things on a daily basis would be helpful.Good Luck

Trying to understand if we should sell now while we can still avoid capital gains or should we hold property as the area continues to become more and more desirable. 

Create a desire to choose your home over the other 10's of thousands and you won't be fighting (as hard) to get your unit booked and noticed.

By the numbers it looks Durham is a more desirable market for an influx of residents across the US - https://www.redfin.com/city/4909/NC/Durham/housing-market

Remember fundamentals like choosing a desirable market and keeping some money in a highly liquid option as reserves like a high interest savings account that should be about 4-5% currently.

The neighboring state of Illinois has a lot higher taxes and less desirable areas in my opinion.  

It is not a highly desirable place in Indy, it is more of a low C/D area.