I'm a huge believer in the "you make money when you buy" philosophy. 

I base this on the "timid land lords raise skinny kids" philosophy from a veteran land lord/friend of mine who manages over 180 units. 

Would certainly encourage you to check them all out!

Very encouraging.

I'd also encourage investors buying occupied properties to have the seller and current tenant complete an estoppel letter.

In general think of it this way, normal pay (2W) wages pays the govt first then expenses, investment income pays expenses first then the govt gets their share.So if you think of the rental as a business (LLC not required), all the expenses are taken out before the govt base is calculated.If the rental has a note, or if there are any repairs, or any other expenses are taken out first, then the remaining amount (the profit) is taxed at a lower rate.One huge benefit of having rental properties is the long term appreciation is only taxed at the sale of the property, or can be put off via 1031 exchange, possibly definitely.I would encourage you to talk to a tax person.

In fact, my philosophy is exactly the opposite of that you are asking because every time a tenant moves I love it because I increase the rents all at one time far more that you want to spend several years and raise the rents a little every year.Every investment calculation and decision needs to be spread over 10 years.

A common investment philosophy for REITs and individuals is investing in construction loans or loans to developers to sit on the debt side and collect interest while the project is completed. 

He then encouraged me to do some 'house hacking' by buying a multifamily and living in one unit while renting out the others to pay for my mortgage.

The founder talked about successful student cases and encouraged people to join their program as students for a few thousand bucks and more... their lower level students get to invest in the deals offered by the higher level of students...and most of the syndications done by higher level students raised funds from lower level students..It really sounds like a multi level marketing for me, especially after I wrote it down.I have several concerns about such education programs:1) are their teaching materials really worth the money?