My main question is, if I don’t plan to do a tremendous amount of work in the new property, but I am willing to do some cosmetic upgrades, does it feel safer to buy something that’s already occupied and has good tenant history… Or some thing on occupied where I can be sure tenant selection is stringent?

Your earnest money deposit should be held by your title company in escrow until closing or termination of the contract.The buyer has the option/right to select the title company unless it is an attorney state, in which case the buyer's attny would select who will do the title work.That being said, until you know the ropes a bit more, the earlier suggestion about speaking with a competent real estate attorney is valuable advice as per @Nicole Holcomb. 

Visit the BP rental calculator at https://www.biggerpockets.com/...You can click that link, or go to the "Tools" menu on BP, and under "Calculators", select "Rental Property".

This led me to select a broker with a strong in-house property management team, because it allows me some synergy when serving those clients.

I sent everyone already scheduled to see the house a link where they could select a specific 10 minute slot during which to visit.  

This is part of the contract for the form of payments. " (1) Tenant must pay all rent timely and without demand, deduction, or offset, except as permitted by law or thislease.(2) Time is of the essence for the payment of rent (strict compliance with rental due dates is required).(3) Unless the parties agree otherwise, Tenant may not pay rent in cash and will pay all rent by (select one ormore): cashier's check electronic payment money order personal check or other meansacceptable to Landlord.

This is a great place to learn and to meet people so take advantage of all the great resources.If you wish to tag someone in the conversation on the forum, type @ followed by their name and then select the name of that person which should appear below the comments box.

With that being said,  if you Go to the Networks tab -> Search Members -> Type Orlando FL -> select Members tab. 

If you click on that, you can select what services you need and it will provide a list of reputable servicemen to complete your task. 

Actually, there are several tax benefits (and strong liability benefits) to buying in a corporation in Canada... best to chat with a knowledgeable accountant before selecting an ownership structure.