Even a good manager needs to be overseen, met with in person, and I like to put eyes on my rentals fairly regularly, since it is my money on the line. 

Many regular agents would not know how to handle this without asking their broker..I assume you contacted the seller after the listing expired, correct?

Alan CeshkerAs most regular posters know, I’ve done many sub tos, wraps, etc. both on the buy side and the sell side, but mostly concerning commercial, not residential property.Here are some of my thoughts….1.

I would also prioritize trying to replace your regular 9-5 job and then gradually increasing your income with more experience.

@Emily Anderson true on the flat 24% tax rate on rental income without the possibility to deduct costs from it.Keep only one thing in mind: rental income is being added to regular taxable income (salary and rental income).So I could deduct costs before ending up with taxable rental income, however for me, it is being added and calculated together with my salary income.That means I'm easily reaching higher tax brackets even after the deductions, while with a flat rate it always stays the same (even if you earn way more rental income).

Landlords should inspect their properties regularly and be aware of what's going on.

It's no longer a secret that most regular job even in tech, has been sent to other countriest.

I see these four rentals providing us a regular stream of income during retirement. 

It's important to go there in person, at the very least do video calls if you can't fly out and be in regular communication with whoever is working on or managing your property.

The purpose would be to rent it out through a property manager just like a regular single family home.