For the modifications, cities generally focus on safety and code compliance, but since you're considering structural changes like wall removal and garage conversions, obtaining permits is key.

With a land trust, the legal ownership remains with the trust, helping to avoid triggering the DOS clause when transferring beneficial interest rather than title.

Depreciation recapture is triggered when a property is sold, requiring the investor to pay taxes on the portion of gain attributed to previously claimed depreciation deductions.

Depending on the lender, you can/should tell them upfront so they can document the LLC in the file so you are sure not to have a due upon sale clause triggered when/if you do transfer into your LLC. #2.

If you are with a cloud brokerage like eXp or Real, you can just move and stay under their umbrella with a new state broker after you complete whatever Illinois needs for reciprocity.If they don't have a TC team, you will need to complete and upload all of the paperwork, but they should have compliance videos for you to do.

Likely, the single-sentence format triggered the filter, and I apologize that we didn’t catch it sooner.

Here is an update : https://chicagorealtor.com/advocacy/advocacy-resources/northwest-housing-preservation-ordinance-issue-summary/The DOH has posted the forms required to be in compliance with the ordinance which means any properties not under contract by 11/9 will need to be pulled off the market and 30-60 days notice must be provided before listing.  

However, strict compliance with IRS rules is essential to avoid penalties and preserve the tax advantages.Best of luck with your investment!

I think it was the BRexit vote that triggered the rush for the door.

Honestly it’s all about opportunity cost.If that additional cost is going to yield you more than it costs; then pull the trigger .If you borrow a down payment, it’s going to reduce your cash on cash return as your mortgage payment is increased.