The 2 year guy is paying much closer to market rent and is more likely to be able to pay market rent if you're going to raise it; you can guarantee the old lady is going to move or default if you bring rent from 8something to $1400.

The business owner should focus on higher paying per hour tasks like raising capital, finding deals, building systems, building the team, networking, etc. 

But if it's a safe, respectable and working class neighborhood that is expected to stay as such, I'll likely opt to refi and raise the rents. 

You raised her well.

Definitely leveraging the momentum to raise money, network, and close on another one before April!

@Brian Pulaski I was born and raised in LI, so I know all about high taxes.

I had about 20 rental doors in 1 1/2 years and this is all while maintaining a full-time job.My approach was basically buy, fix up, raise rents, keep for a couple of years and sell which I did with many of my rental units.

The goal of my post is to just raise some basic awareness.

Put some work into it, make upgrades, raise rents over time, cash-out refinance in a few years or sooner if you can, and hold it forever.

If that would be difficult, I would say raise the rent a little at a time and let him stay.