I put in my lease that I only accept rent via online payment service.

Does anyone use a good book keeper on line that I could pay to set it up and occasionally use?

If you have contractors you like doing business with all simple repairs can be paid online while you have your property manager look over the work.

Michael Gessner none to be honest I just been taking online classes.

What are some online websites/ software platforms for RE portfolio managing?

I think your best bet for something u can do right now would be to attend local metups in your area. network to other investors. try to develop a relationship with your local credit unions.

Most lenders have a 2 year minimum seasoning on BKs.Honestly, IMO, his best bet is to contact the lender (NOT the servicer, but the LENDER), and throw himself at their mercy for a loan modification. 

Honestly man most of those companies, they make more money then they do on there real estate portfolios, and they use on online platform and you have a "coach" who has very basic knowledge. 

I bet your instincts are telling you no while the numbers are telling you yes.

In your example, it's a complete change in the buyer, so I'd be willing to bet that the bank is going to take issue with it.