There are some creative options I bet you could think of with family though.

I suggest to never bet on appreciation.

You pay for it, you work for it, you have substantial risk involved, the only person who should benefit is you.  

To be fair, he has been involved in real estate for decades (owned a manufactured homes company, flipped homes for a few years, etc.), but he is absolutely convinced that there's no way I could buy lower end homes in my city to rent without ending up bankrupt.

A friend recently had a tenant through the tenant's agent want to buy their house, and it fell through even with the agent involved as the tenant didn't qualify for the financing. 

The bet is that the people will continue to rise every day and go to work, which we will, so long as we are poor enough.

While many agree the accredited status is high, there are reasons for it (namely to protect everyone involved, especially the investor) and the SEC has also allowed non-accredited/sophisticated folks to invest in these types of deals through a different structure - the 506(b).It is 100% okay for you to reach out to Sponsors or other people putting together the deals you're referring to.

I bet there's a hard money lender in your area who would look at it to give you short-term, bridge financing. 

@Jake Parks - If you're pooling money together and providing a return for people/there is an expectation of profit for someone else and that other party is not involved in the decision making/management of the deal , then you are creating a security and the answer to your question is a resounding yes.The big thing you have in your favor with partnering up with family and friends is that you have a relationship with these people already and that's the biggest thing that the SEC is looking for.

There aren't really any formulas for this, your best bet might be to look at the pictures in rental comps other than that I would estimate the difference to be about $100 in rent for every $1000 of rental value if everything in a non-updated unit is clean, usable and looks reasonably nice.