Noah,There are a lot of places in Orlando that offer good deals on cash flow properties. 

However, they will not be as good as agency loans.

If you’re working with a tax professional ask them to do a tax projection for you with one scenario assuming you sell all 5 today and the other assuming you only sold 2 today.With the tax projection you’ll now have a good estimate of what your tax situation will look like and can make decision based on that.Maybe you can consider selling your portfolio and doing an installment sale, this won’t help on the depreciation recapture but it would help spread the gain over multiple years.Each strategy has pros and cons, if you want to rip the bandaid off an be done cold turkey (or warm turkey if you’re into that) there most likely will be a large tax hit but less headache holding them longer.

. $790k turning into a multimillion property seems like it's too good to be true.

Does anyone have a rule of thumb for how much cashflow one should be getting for every million dollars of debt on real estate?

Good to hear about the combination.  

Working for one for free in exchange for guidance would be a good idea, but I would be skeptical of somebody who wanted to charge me $4,000 of my $5,000 starting budget. 

They have been good guests and have already paid me in advance.

But if you have a good rep, you should be able to close files in 15 days. 

Since you were smart to house hack a 4, I would see what you can get for a 2 in good shape, not a BRRRR or rehab (too much work when you are new).