My biggest goal would be to take a relatively cautious, conservative approach and learn as I go.

I would be very cautious doing CFD's, as in most states they are now treated like a traditional mortgage so all it does it adds the risk to you. 

There is too much risk that the deal could fall apart in 90 days.In addition, if you are selling a short sale, cautious title companies require so many disclosures to the shorting lender, that in some areas, same day sales of short sales are all but dead.

I also put in 10% to 20% contingency on top of my numbers to be extra cautious. 

Since you mentioned multifamily in Tampa, I would just add to be cautious when looking for properties as in that area there are so many that are done without permits, and VA is strict with each unit having it's own water and electric meters.

Only thing to be cautious of is going too crazy with colors that you might deter people!

There are good deals to be had in Saint John for sure but having lived here most of my life you have to be cautious on both location and properties.

I'm cautiously optimistic that one of the options will work. 

I don't know all the details, it was just info through an investor friend, but I (and recommend all) stay cautious ab investing  in the St.

I am glad to see you are being so cautious with screening.