If you want immediate cash flow CA is not the best bet.

Have others bet on cities like Cleveland, Milwaukee, Minneapolis, etc given the relatively low climate threats in these areas?

@Troy Scottaline a safe bet is you can get somewhere from 6-8% cash on cash return after all expenses are paid on your investments.So if you want to live on over $100,000K per year and do nothing but manage rentals or manage a property manager you will need well over $1,000,000 to invest.

"No trips to the cabin during the stay" won't win a chargeback dispute. 

If we did win the bid do the current owners have the right/ability to stay in the house?

But, you must have the money required by the site within X hours of the winning bid.

Buy the book "how to win friends and influence people" https://www.amazon.com/How-Win...   

@Isoke CraigBeside purchase price, there are other factors that make for a strong offer: Type of financing - convention or cash are better for a seller than FHA and VAEarnest Money - consider higher than 1% of purchase priceOption fee- higher the better - more incentive for the seller if you back outShort option period - I win offers with 3-5 days to inspectPurchase the title policyThe list goes on. 

Just starting out. I am looking to have a fourplex built to reside in one and create cash flow from the other units. Furthermore I am looking to also Brrr the property in the future and continue investing and building...

They could probably win a judgement against you to collect delinquent rent or even sue for damages.