Nothing crazy, but I have already hired a bookkeeper.

We COULD do this, however, we would have to charge like a book keeper / CPA to do this as missing a mortgage payment would be very very bad.  

Bookkeeping and keeping the back end of business sharp and accurate is beginning to take time away from growth and I know this is not the best use of my time.

I have 2 handymen that I can call to do maintenance that I pay $10/hr, and I have a bookkeeper that works part time.

If that's the case, and going into a judicial foreclosure, I can certainly see the borrower's attorney raising the issue as to redemptive rights and I'd say any judge would like grant the request, IMO.Your last paragraph isn't real clear, if they are using prearranged deed agreements, I don't care how big they are, not a good idea, in fact the bigger you are the more you'd better conform or accept the liability consequences.I'd prefer setting up a sister entity that would buy the property and then lease back, after a period to qualify, some inter office bookkeeping could take care of the financing, just make a new loan.

I have learned that it may be beneficial to itemize everything carefully with quality bookkeeping.

Being organized with your documents and bookkeeping will go a long way to smoothen out a potentially bumpy tax season.

Also look into property management companies that are hiring this will give you a hands on approach in dealing with tenants and dealing with bookkeeping as well as learning typical monthly expenses. good luck hope this helps

Check this one out on excellent bookkeeping. 

It makes book keeping much easier.