Although you could probably find better investments on paper, vacancy & turnover expenses are some of the most costly parts of owning investment property, and very difficult to forecast with perfect accuracy.

Strictly speaking from a financial point of view multi family's almost always make more sense unless your walking into some equity in a single family. creating a 5 year goal/plan makes perfect sense actually. thanks. 

If this works, it would be a perfect way for him to get started in real estate by learning how to house-hack and also building equity while I will get a lower down payment into a high cashflow property.

There is no perfect software out there.

What is the lowest up front amount we could get away with? 

You aren't going to find perfect.

Seams aren't perfect but are not bad now, looks like it will end up being a regular maintenance task but at least I don't have to pull up the baseboards anymore!

He even made a solid friendship with one of his tenants, who now handles some of the property managment for him.These neighborhoods are perfect if you want a vibrant urban lifestyle while also reaping strong rental returns.

Plus, working on properties close to home will give you the insights you need for when you pivot to rentals.You’re in the perfect place for advice, tips, and a community that’s got your back.

This makes perfect sense in today’s experience-driven world.