I would like to set it up so that I can basically hand reports with receipts to my tax guy and be done with it. 

.** You should also look into any potential property tax increases associated with this change.

When investing in real estate, don't overlook local and state taxes.

Wanting to move these properties into an LLC but I find out we have to pay taxes (7%) on the transfer equivalent to the mortgage balance.

In general, expenses related to the purchase or improvement of a rental property can be deductible, but the treatment of these expenses may vary depending on the nature of the expense and applicable tax laws. 

They have shown me tax returns for the business. - I asked for 3 months' bank statements and have about 20k liquid- 16 derogatory remarks on credit report- (I feel dumb for even asking considering this)Here is the kicker:- they own a restaurant and already said "How would you feel if there were occasional workers that stayed here?"

Used to be about $1,300/month, but after the hurricane, insurance has doubled and property taxes have taken a dent on that.

I just sold a spec, I built a house for my self last year and finished a spec this year, I bough the lots at tax sale, and I was the GC, HVAC, Tile, Flooring, Cabinet, Painter, and Misc. guy, made a nice profit, but the crappy part is taxes, its like a flip, short term gains. good luck!

It's a good idea to talk to legal and financial experts about taxes, insurance, liability, rental agreements, and managing your finances.

Look at your monthly payment (PITI = Principal,Interest, Taxes, Insurance) + HOA + (other maintenance fees if any) and if this amount is less than what you charge for rent (whether its Long, Mid, or Short Term rentals) and you are happy with the positive cash flow, then yes.Or maybe you're breaking even with the condo but you have  knowledge that the condo will explode in value due to some business/attraction/law/policy that will prop-up the sales price in the near future, then yes.Really, it boils down to what your goals are for this first investment.