I’m interested in what others say however if it were practical I would think we would all have jumped on this by now.  

His practice covers the state of Florida...

Since rent control is illegal under IL state law nothing can change a landlords ability to do that. 

Not only is this good practice, but over time you will earn their respect, which means you will earn their investment funds.

But if your neighborhood has lots of garage conversions, then that would lead me to believe you don't need that garage and that it's normal practice to convert the garage.  

Well, that is a good question, but it comes down to difference of opinion, and him taking control of everything I do.

My guess is there is a due on sale clause.Now you broker may be speaking from a practical sense, knowing the risks is minuscule (for both issues) so he glosses over them.

Rent control, crazy laws anti landlords and other things makes it hard to enjoy your investment. 

Would you allow someone to "buy" a property, for $0.00, and you pay 100% of it for them, yet have 0 control of it, just a hope and prayer that it all goes good? 

I was very naïve in the beginning but my mentor taught me to take control of situations, even if that means calling/texting someone that is involved in the deal once a day for 30 days straight (I have done this with a lender recently because the deal was being put on the back burner).