Hi,Its recently come to my attention that one of the trustees of our condo association is short-term leasing their unit in violation of our bylaws (which require rentals to be at least 1YR terms). 

To ensure success you will definitely want to associate with like-minded people, people with experience and who are already doing what it is you want to do, and people who inspire you… not naysayers, negative people, nor critics.

Both of those property types/approaches have added risks and pitfalls associated with them, in my experience. 

To ensure success you will definitely want to associate with like-minded people, people with experience and who are already doing what it is you want to do, and people who inspire you… not naysayers, negative people, nor critics.

Also search for them on NARPM (it's an association for PMs)

Check out the version with class tracking that allows you to associate each transaction with a particular property.

So a conventional lender - are they associated with a bank, CU, independent lender or are they a mortgage broker working with many lenders?

Most landlords aren't going to want to do that for a few reasons, one is the risk associated with having strangers going in and out of their property, the extra wear and tear plus damage that can occur from guests behaving badly. 

Starting pay is actually better than many college degree jobs.

This gives you a degree of asset protection (depending on the state) which is the main point of an LLC.