I highly recommend interviewing multiple contractors and ask them for references. 

A high occupancy does not guarantee the lost revenue.

They have to be tweaked on a regular bases and most of the time it is due to it throwing out some crazy high ridiculous prices for some dates.

Am I going to make money on it, is there a value you ad opportunity so that I can fix it up increase the rents and thus increase the value of the property.

It's highly debatable whether $50k can be considered "reasonable compensation" if you make $200k from commissions on the properties you sell yourself (as opposed to a split with your agents).

- Get properties under contract for way under market value.

I would get a high quality sleeper sofa.

Every investor has a different approach, but I personally buy my rentals the same way I buy my flips..at a deep discount using hard/private money, then refinance with a rate-and-term loan to secure a lowest interest rate.Ultimately, it comes down to your goals, risk tolerance, and ability to find value-add opportunities.

Medical Payments: Provides coverage for an injury suffered on the premises.

30 - How high will the ceilings be?