With that in mind, I’m considering purchasing four rental units over the next four years to build a stream of income that could help supplement my retirement by age 68.The challenge I’m facing is that the deals I’ve come across so far don’t make financial sense.

The challenge again, is the prices around here.

We understand that tax complexities can be challenging, but our experience shows that many of these barriers can be overcome with a strong local team.

Value and rents should eventually increase to turn cashflow positive and build your wealth.You're next learning experience will be, now that you are out of day-to-day management, how will you be able to handle the inevitable expense challenges?

What are the challenges of passive investing as opposed to traditional real estate investing? 

Challenges?

Also deleting duplicate posts, not sure how you could make it so duplicates self delete or don't post for those of us with tech challenges....

Quote from @Jeff Rich: It would be great to have the app back. 2 votes up, I'm 100% mobile and the site on browser mobile is umm "challenging"  Maybe at least make the site more mobile friendly?

However I did note that houses are mostly really old, e.g. 100 years or older... any idea if this poses challenges in things like lead paint presence, outdated wiring, rusty plumbing, etc., or have many of the homes already been updated?   

All the youth have left, maybe the elders are still there or they are deceased and the children don't want the property.