To answer your first question, yes, you will have to pay Realty Transfer Tax on this transfer of real estate. The tax would be assessed on your entire share of the property (i.e. 1/2 of the total fair market value).
In response to your second question, yes, there are plenty of other things to think about. A couple of them are:
1. Your LLC will be subject to a Capital Stock Tax however if you set up a General Partnership, with the LLC as the General Partner, you could get the same liability protection and at the same time minimize the tax; and
2. By putting all of the properties in the same business entity, you are not insulating each asset from the liabilities of the others.
It is always smart to consult both an Accountant and an Attorney before taking on the kinds of projects that you are contemplating. Feel free to call my office (412-904-5305) for further advice or for a referral to an Accountant.