I cant speak for every deal they have ever done, but I will say that any deals That I was involved in with safeguard and there was any issue whatsoever they jumped in and worked diligently to solve the issue as if it was there own money. 

I am VERY involved in all aspects of my business...and, although I trust, I also know how everything is done and verify most things.

There is no seasoning requirement involved since the property isn't a short sale and it isn't someone buying REO from a bank with a seasoning requirement.

Anything involving a service animal and ADA should be directly consulting an attorney on the matter as every case is different. 

who are involved in wholesaling or other real estate ventures.

Lastly more to my point - I thought you worked for a MF syndication in the past that I was not sure but wanted to mention and that you are not just someone coming off the street having never been involved in a deal (unlike a lot of others).  

There are variables involved, and there’s of course skill and effort required not just calls.

Converting your condo into an investment property and transferring it into an LLC is a smart move for liability protection.You’re correct that retitling the property involves Chicago’s transfer tax, which can be substantial.

It’s also important to consider if the work involved aligns with your lifestyle and goals.

And having a property manager does not mean that you’re not directly involved with a lot of issues with your properties.Given your situation I might rather suggest a REIT investment where you get exposure to the category, but not have to deal with such a large portfolio, or just get your feet wet and see if you like being a landlord by buying a couple of properties  Randy