Usually the department that you need to speak with will be called something like loss mitigation. 

Can anyone speak from experience or expertise about what issues I might have by leasing the property to three parties, given I respect the occupancy limit?

@Matt Ruttenberg Generally speaking there are 2 main types of loans for investors: “Conventional” and “Portfolio”Conventional - I'll define these as loans that come from Fannie Mae and Freddie Mac (if you recognize those names).

@Jordan Jaramillo you might have found your solution by now but I would highly suggest in speaking with your lender about refinancing AFTER you purchase with cash to make sure you can do that and how much you will get.  

This is not going to be the best advice for each and every investor in every state, however, generally speaking, it is the best entity to flip from.

Hi- can someone speak to requirements by city to do either short term or traditional rentals? 

No one that has ever tried to use a home warranty for a repair speaks highly of them. 

Generally speaking we target properties that are $250k and lower.  

Generally speaking yes.

I know you're not going to like this answer but you may need to speak with a good CPA.