If it's on the MLS, investors have direct access to it via the listing agent or their own agent, so why would be able to buy it cheap and the resell it into the same market that it's already sitting for sale on?

However, it's always a good idea to address any potential issues upfront to avoid complications during the sales process.In short, if your property is currently insured and meets all building codes, replacing the secondary roof may not be necessary.

Would it be best for me to talk to a lender and figure out what I can make work before looking for properties?

Every market has opportunity in the right places with the right deals.1-4 units follow the market appreciation through sales comps. 5+ units you start getting into forced appreciation through NOI approach. 

Firstly, I'm interested in hearing opinions, facts and figures related to the current market conditions.

Unless you are doing all of the maintenance yourself, figure about 5k yearly for touching up paint, repairing misc. items the guests break, bikes, kayaks, BBQ grill, pool maintenance, lawn service, pest control, replace TV remotes every time someone checks out. 

It is a pretty popular restaurant so I am sure sales would do well.

I don't know, lately I've been thinking if I would still want to be doing this whole landlord thing in the future and therefore trying to figure out if there was an tax convenient way of liquidating all rental properties and live off a brokerage portfolio.

I'm assuming this percentage varies in every market so Im trying to figure out what mine is and what the "expenses" of the 3 above generally are. 

If you can figure out a specific strategy and be THE guy in the space, it could work out.