I think this is a more challenging question than it seems.

I am new to real estate and starting my journey to set up and build a real estate portfolio that I can pass on to my children.

It's hard to say without knowing the details.As an aside, the fact that he's living with a woman and her children today means nothing.

The challenge is convincing one's partner to move into it :)

Challenges?

It's important to work with someone who has firsthand experience with the challenges and rewards that investors encounter.

Also, in a 1031 the seller cannot take possession of the funds so you giving him the downpayment to do repairs would be challenging.

Challenges?

I see what you’re saying about cash flow, and I agree—rising prices are a major challenge for investors and buyers.

The experience of the housing provider is going to be the real challenge to getting you a set of keys to move in with...they have to qualify, pass inspection, sign a bunch of paperwork, and finally lease up and send everything into LMH.