Either titled directly in the trust or as a beneficiary of whatever other entity you choose to title the properties in ... land trust, corp, LLC. 

Perhaps your first step is buy your primary first 3.bed / 2 bath SFH in the best neighborhood you can afford.

Hearing horror stories of getting bad renters out and the damages they do to the home, I'm intimidated to rent out my home and proceed with buying a new home to live in and update.  Those who have had experience, were...

But it’s THEM making the decision and THEY are the one’s doing the choosing – I’m simply providing the options.Let me end by saying there are many more successful and seasoned Investors out there who would disagree with me.

Of course, I know up front from “pre-qualifying” him over the phone earlier what the solution is, but rather than me telling him the solution, I allow HIM to choose it himself.

If priced correctly, 1 and 3 bed apartments also shouldn't be terribly difficult to rent (which is why it's so critical to buy right!)

You referenced other cash reserve, I do have some other funds to use towards whatever home we choose next so we aren't banking on these funds.  

No matter what you hear about Wholesaling our services are desperately needed in every community and if you choose this direction be proud to serve your community in this way. 

I own three properties total and I am currently on my 2nd house hack.Deal #1: Desc: House HackType: CondoYear: 2004Location: Uptown neighborhood of ChicagoDeal #2: Desc: House HackType: SFH (3 bed, 2, bath)Year: 2012Location: La Grange, ILDeal #3Desc: Short Sale, CashType: CondoYear: 2013Location, La Grange Park, ILMy goal is to build a portfolio of properties that cashflow 100K/year.

It's the same reason that Subway would choose to lease the space rather than buy their own building - lack of capital (or better use for capital).