In 2014 I was able to get a loan modification on a rental and of course I got 1099'd for the debt reduction.  

Depends on the note as Jay mentioned, non-judicial states will be quicker but federal laws require notice, demands, collection records, modification allowances, redemptions and 120 days before you can proceed.

Assuming you have a rental or lease agreement, any time a tenant communicates with you regarding something that potentially modifies the lease, your response should be that, "Per the lease, modifications are invalid unless in writing and signed by both parties.  

You may be able to negotiate a modification with the fist lien holder after foreclosure, but its a risky gambit at best.  

The home was rented but the rental income left me with a $430 a month shortage.I applied for a loan modification twice, once in 20011 and once in 20012 and was denied both times.

Yes, servicing is a cost of business and effects the ROI, the discounts I usually work at, $15.00 won't break my return.......it's all relevant.But, if you collect on a small note, I suggest you let an attorney tackle notices of default or hints to modifications......if all goes well you should have no issue.While you can hold a note long term, I'd rather see them pay it off as quickly as possible which increases your ROI and gets you ready for the next deal with money in hand.

Modification, servicing, negotiating with the borrower, etc may require licensure IF the note in question is an owner occupied mortgage note.  

There are companies that prepair the contract for you; (business-in-a-box), and you can make modifications.

I guess is that the modifications and improvements that will need to be made are going to cost enough that you are better off owning the house?

Modifications and reinstatements are not going to be similar events among loans at all.