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.

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

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.

I am really trying to figure out how to put in a bid on the Baltimore City tax sale (coming up in May).

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

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. 

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.