In your case you have a lot of losses in the time you own the property but these losses transfer through to your personal tax return, so you can recover some of it and not have to count the full nominal amount.

For example simply filing a quit claim deed to transfer the properties to one entity (existing or new) would be easiest however that may not be an option if you have loans in place... 

I believe trusts can be helpful to transfer the deeds without probate. 

So - you transferred it into a boutique motel?

Once approved, we offer a lease to the tenants, collect first months rent (which we retain) and security deposit (payable to owner)  We also make sure they have utilities transferred and renter insurance in place before obtaining keys for move in. 

He lived in it for 3 years while attending college, and now I am considering transferring it into an LLC.  

I took a transfer with Lockheed and landed there from Atlanta.

If the title transfers, that's a sale and will cause a tax event.

If I am transferring 2 properties from a co-owned LLC to a personally owned S-corp, do I have to pay any taxes on that transfer?

I have been told to use Baselane so that they can ACH transfer for free, and that baselane also gives me 4.5% APR for my money saved there (i.e. security deposits, etc.)However, I don't like Baselane's withdrawal limits, and also how long it would take for baselane to transfer money to my primary checking accounts, at JP Morgan.