The riskiest strategies that have the highest projected income are flipping and short-term rentals, behind that, BRRRRing, and behind that is turn-key cash flowing long term rentals.

If the interest rates come down, I can transfer the property back to my personal name, refinance, and then transfer the property again to an LLC or trust.Second and most important thing, I would like to get an idea of what type of property to purchase that best suits for STR in Chicago area , near by states like WI or MI also I am fine as long as it is closed to Chicago. 

Is there any standard paperwork I need to sign with a troublesome tenant who, after long negotiations, moved out on time?

So if you can target a little nicer property you can enjoy better interest rates for your long term hold. 

Nicholas, as long as you live in one of the units for at least one year, then you should qualify for an FHA loan.

Or long term property management? 

. - the best market is one that has properties you want to hold long term.  

I am on the same boat and looking for a LTR (long term rental) in Hagerstown with steady cash flow.

Long term?

While seller financing is less common with flips, there is no real reason it can't be used, as long as it satisfy your needs and the sellers.