I'm a retired engineer and have been successfully using income from these houses to support my retirement without dipping into retirement savings.I'm transitioning my business from rentals to a franchise and would consider selling one of my houses (5 br/4 ba - the other houses my son while he's still attending).

I signed up for Baselane today after switching from Mercury for my business account (LLC).

That's just the nature of this business. 

I don't have any specifics but as someone who is into tech, accounting/finance, and a consultant to grow businesses.

The IRS doesn't trust you to report accurate information, so the 1099 from the property manager is checked against your filing.Any company that does more than $600 in business with you should issue a 1099.

I live in Boston, but I was advised to start my real estate business elsewhere as Boston is very competitive.

It's always important to screen anyone you are doing business with. 

- The market is in a little bit of a lull right now (buyers market), its a great time to buy, but slower time to sell (my primary business is flipping houses) I can supplement my flipping business by providing project management services/consulting, helping investors find discounted properties, etc. etc.

People can remotely access the homes using your digital lockboxes, if you have them.

I normally advise that people start a business as a sole propeitor in their first year.If it is successful and something you want to continue, then have a conversation regarding entities.