Brokers are willing to do this because they only get paid a commission when a property is sold so they’ll work with tons of investors and find their ideal properties to maximise their commissions.

Ideally we want from a duplex up to a ~10-unit building.   

Which, arguably, should be the case anyway, since in the current situation the common areas are paid for by at least one tenant, but if you're going to be living in one of the units and especially if you think the common areas would be on your meter, then you may not really care.The gist of your question is really, what's "good enough to consider the building a 4-family", and that's a question you really need to pose to the Providence Building Department - ideally in person, if you can swing it.

Ideally, you're creating enough value to refi in a year or two and pull out your initial investment.

Hey also check out the Deal Machine... it's super ideal for people looking  to drive for dollars

Ideally we'd like a multi-family, but we know that it is rather limited in Lithia, FL, so we are open to single family homes as well. 

These go hand in hand as it will help you identify what the ideal (not perfect investment because there is no such thing) investment looks like.

This would have me paying less taxes, paying less in income based student loan repayments (which ideally would be forgiven in 5 years after working an attending.

My ideal scenario would be to attack fixer uppers in one market and turn it over to a management team.

I'd ideally like a combination of both, but I guess it's even harder to have your cake and eat it too.