I set up my mortgages so that they bring in enough money to be offset by depreciation.

Railing and steps which can cause a mortgage rejection on buyers part.

I'd recommend talking to a mortgage broker who is licensed in your state. 

Definitely not enough to retire on now, but it should go to 23-25k/month in 7-9 years when some of the 15 year mortgages are paid off.

There is a mortgage contingency on the contract.

I've thought about buying on the high end of what I could afford (in highly desirable areas) in the hopes the property values will climb.Should I forgo financing entirely and buy something "cheap" that I can pay in cash or take a minimal mortgage on?

My market is seasonal and I was begging for enough revenue just to cover my mortgage so I wouldn't have to pay my own rent AND a mortgage. 

@Nick BednarczykI think people also need to understand that fed rates are not directly correlated to mortgage ratesMortgage rates are more in line with the 10 year treasury which could remain high if we continue to spend money like a drunken sailor

You get the benefit of the homestead exemption plus having tenants paying some of the mortgage (if you can find a fairly priced property...not easy in south Florida!). 

Canadian investors have several financing options, such as mortgages, private lenders, cross-border financing, and partnerships.