When I established my investor services business in 2005, I posed a similar question to numerous experienced property managers.

Eliminate debt, establish a budget, and save.

The fact that this sponsor used investor money to gamble on high yield unsecured notes leaves a bad taste in my mouth.  

Instead, focus on establishing an authority in your area and building an audience.

When would you suggest to establish an LLC for your portfolio?

I'm assuming you need an established working relationship with said lender.

Establish a Joint Ownership Entity: You could form an LLC or partnership for future purchases.

You can focus on properties that have strong rental potential to generate steady cash flow, helping you pay down the mortgages over time.Once you’ve established a solid cash flow and built equity, you can scale by adding more properties gradually.

Once you become more established, have a large net worth, etc. you may want to consider more sophisticated trusts that can cost you up to $45,000.

In the Bloomington-Indianapolis market, establishing these connections can provide you with off-market opportunities, mentoring, and invaluable advice from seasoned pros.