I believe Orlando may be a bit saturated with people who have a similar strategy and goal in mind so the competition may be higher.

Best case scenario: You buy in the off-market later this year when competition is at it's relative lowest, and then interest rates drop at some point in the next few years, and you can refinance. 

Lastly, as the point of number 3 with a lot of offers, know that there will be a lot of offers and if that is the case, your COE "close of escrow" will want to be shorten to be competitive, but those assumptions can take 30+ days to close (typically 35-40 days).

There are some great competitive advantages when entering from OOS.

What's your competitive advantage?

The cost of UDFI is generally nominal, and should erase only a small fraction of the boost in return that the use of leverage creates.So:  Make an all cash purchase and receive 10% return or make a leveraged purchase, pay tax on UDFI, and make 13% return. 

I can understand the reasoning behind only purchasing off market properties - less competition for buyer and that often means they get more leverage.

Plus there is so much competition from tons of people trying to get into wholesaling, not to mention the big players already getting the lions share.

At this point, I'd recommend studying your competition (what are they offering that you're not?)

Real estate is a long game, and getting a good asking price when the demand isn't as competitive because most people have similar thoughts to yours - might be worthwhile to take on the investment.