I'm looking to start my first STR in the Chicago suburbs near O'Hare airport, but I'm a little confused about how reliable my information is.

My plan is to buy a property, whether it be single family home or multi unit, n either rent it out once I move or if a multi unit, rent out the other unit(s).

My plan is to pay that off ASAP and get a HELOC to maybe buy a Multi-Family unit. 

My lender thinks he can get me approved for a mortgage to buy it as a SFH, but even if I could - I don't have $180K for the down payment.The only idea I have is to make a list of every rich person I know and take each one to lunch to pitch and hope that one would be willing to lend me 900k at going interest rates, collateralized by the property.

Their overall goal is to hold onto the property and bequeath to the next generation.

Any time you have a claim it is going to be review by an adjuster whos job it is to determine if the claim should be covered or denied.  

You get long term finance and if one renter goes out you still could possibly have cash flow to pay the note.Another option is to buy a house in stage zero of a new home development where homes are just going up.

Now our plan is to purchase a second property and house hack that as well but we’re being told we have to wait for our refi to ‘Season’ before we buy another property as owner occupied.

The plan is to maintain for two years pay off a large percentage of the debt then repeat the process.

I think the best play is to go conventional at 70% LTV, refi after 1.5-2 years and go CMHC for long term.What are your thoughts?