If you buy yourself a vacation rental in the right foreign country, you'd invest much less than you'd have to in Florida to make the same rental income.

Additionally, it aids in evaluating the feasibility of projects, allowing you to focus on the most profitable opportunities.

Feel free to ask anything additional if you need.  

We are largely looking to gain some tax advantages through investment properties to help offset the W-2 income.

You got bad advice from your prior accountant.You received rental income and it should have been reported.it seems like maybe he was lazy and/or doesn't understand rental concepts.The only exception is if he is paying 'under-market' for rent in which case the property would be considered personal use.I would fix the issue and charge him market rent. 

The remainder - your net operating income, divided by your purchase price is your return. 

I have a Series LLC I use to collect income for my consulting business, but the income goes to my personal checking account.

Given your situation and concerns, here's a breakdown of considerations and advice:Pros of Renting Out Current Home and Buying a New Primary Home:Living Condition Upgrade: Moving to a larger, newer home with boutique features can improve your living space.Rental Market: West Town in Chicago generally has a strong rental market, which could provide good rental income from your current home.Portfolio Diversification: Adding another property to your real estate portfolio can enhance diversification and potentially increase long-term wealth through property appreciation and rental income.Cons and Concerns:Interest Rate: The current interest rate of 7% on a new mortgage is high, and there's uncertainty about future rate decreases.

You want to have an income qualification such 2 - 4 times the gross rent to qualify for the unit.

Pulling out of building additional buildings we had planned.i.