If you sold it for $500K (after expenses) and invested it in a savings account (or some in a RRSP or TFSA-up to your limit), even at 4%, you'd get $20K a year.Also what province is it in? 

Here are a few strategies to consider for funding a down payment:Partnering: Like Gregory mentioned, finding a partner who can contribute to the down payment in exchange for equity or a profit share is a solid option.HELOC or Cash-Out Refi: If you have equity in your home or another property, a home equity line of credit (HELOC) or cash-out refinance can provide the funds you need.Private Money: Reach out to friends, family, or private investors who may be interested in lending you the down payment with a promissory note.Seller Second: In some cases, the seller might agree to finance a portion of the down payment as a second mortgage.Live Frugally and Save: It takes time, but reducing expenses and setting aside funds from your income is a tried-and-true method.The right approach depends on your situation and deal structure, but a mix of creativity and resourcefulness can go a long way.

We're looking to transfer this into an LLC for liability purposes.From what I can tell, the best way to do this is to retitle the property, pay Chicago's expensive retitling tax, and set up an operating agreement, all of which likely requires a real estate lawyer (what $ base do we use on the tax, given we aren't selling it to ourselves, just transferring it?). 

That’s correct, a foreigner can buy property through a Mexican corporation, which is a great option for those investing in multiple properties or running a rental business.Key Points I'd like to add to your post:Setup Costs: $1,500–$3,000 USD.Ongoing Costs: $1,000–$2,000 USD/year for accounting and tax filings.Benefits: Allows tax deductions for expenses like maintenance, repairs, and management.Best for: Multiple properties or income-generating investments.For a single property for personal use, a fideicomiso is often simpler and more cost-effective due to its lower maintenance requirements and feesUltimately, choosing between a corporation and a fideicomiso comes down to your investment strategy.

Is anyone flipping in a market where this is "average"? 

And best part, all the offsets to it could readily make it a net-0 added expense to tax payers.

He tells you to pay him $5,000 (or much more) to learn all the "secrets" that made him wealth, but then he doesn't tell you that his "secret" was to increase earnings, reduce expenses, save up and invest.

However, after accounting for long-term capital gains tax and other expenses, you would be left with $150k which is important to budget and account for.

My wife and I have overhauled our personal budget to reflect the 'pay yourself first' approach (allocate in order: income comes in -> invest -> donate -> fixed expenses -> variable expenses -> fun $$).We are looking to see what experienced people generally recommend for a holding tank for that 'invest' allocation while we target our first real estate deal.What financial vehicles have you guys used that works well for this?

Research market rents, carefully calculate expenses, and ensure you have a solid lease agreement.