I'd wager heavily that it never comes up.

Now it might not be a bad strategy to utilize, but I personally have never done it.I would wager to say that MANY MANY realtors wouldn't go for it, be skeptical, or claim what you are doing is illegal.So you would spend the majority of your time educating individuals.Just my $.02 worth.

I asked him if he'd like to make a friendly wager and we agreed on $20.00 (I wanted to make it $50).

If they borrow more than they can afford to finance those properties, then they risk creating a crash.Now ponder this headline today in the Wall Street JournalHouse Money: Wall Street Is Raising More Cash Than Ever for its Rental-Home GambitInvestors wager that high prices, higher mortgage rates and skimpy inventory are making homeownership harder for individuals and familiesSo I would say that the signs are pointing to a bubble.

Unless he specializes in landlord/tenant law, I'd wager that most knowledgeable landlords have a better immediate grasp of those areas of the law than he does.

Look at this situation like a poker wager.

I will confirm utilities are back in my name tomorrow but I would wager good money they are. 

I think we both know whats right for us, though due to your experience I'd wager you know a little better.

I'd wager the Zillow ones are not up to date.

I would wager that a CPA could find more deductions and also provide peace of mind that your taxes are accurate, especially when this is new to you.Check with @Adam Hardy  , CPA at Jenson & Co in Maple Grove.