I work with a few private capital sources who finance Wisconsin investors (Milwaukee included) on both flips and long-term holds.

Perhaps you have capital to offer?

Realism of Your $20k GoalYou are right to point out that pulling all capital is not easy, especially with a cosmetic rehab. 

Right now, I don’t have a lot of capital to invest, but I understand that it’s still possible to start in real estate with little to no money as long as you have the right knowledge and resources.

A reminder that real estate investing requires patience and capital discipline.

I am a Capital Raiser for B and C class, value add, Multifamily Properties, ideally 20+ doors.

Quote from @Drago Stanimirovic: Most investors hit their ceiling because of capital, not opportunity.

However, from what it seems from your and Greg's replies, I am understanding that regardless of how we structure it and whether or not we ask the other members/partners to pay us anything for managing the business, we will still violate securities law by using our personal time and resources to invest a pool of money that includes other people's capital.

- Time Capital Bookkeeping (REI myself since 2019)

Depending on your other income, short-term vs. long-term strategies can have very different tax implications, and many people get into real estate investing precisely because of how it interacts with their overall financial picture.Since you guys are planning flips now and rentals later, the tax setup matters more than most people realize.For flips, the IRS treats everything as active income, not capital gains, so once you’re doing more than a deal or two a year, you’ll want an S Corp (or LLC taxed as one) to avoid paying more self-employment tax than you need to.