To maximize the number of transactions you’re involved in you will need to:Be Top of Mind when they think about moving - which requires consistent reminders.Be seen as an Expert – which requires a consistent message and Evidence of Success storiesGain their Trust – which requires communicating integritySo, start out by listing everyone you know in an Excel spreadsheet.

Still has lots of belongings (including a boat) in a large shed on the property... could imply intention to move back, or a desire to not have to deal with it and possible interest in having help getting rid of all this stuff3.

The biggest thing with 5+ units is everything is more expensive, and the inspection requirements (depending on the municipality) are often more rigorous.

I think I will not let him make this upgrade as a 5 year payoff would require over $100/month additional rent.  

A DSCR loan is going to require more down, have high fees at closing, a higher interest rate, a pre-payment penalty, and will require you to have cash reserves that you likely don't have at the moment.

So, coming up with more capital to invest in another property requires some creative thinking.

We actually just had several go in on Livingston ave on the west side where I'd not normally think would be desirable, but they look great and really brought the block up.So I'm a huge fan personally from seeing them go up in my own area.  

What documents do they require, what credit scores do they allow, how do they verify previous rental history, etc.?

Syndications are great for truly passive income, offering tax benefits and diversification, but require high minimum investments and long-term commitments.

The lease should have a provision that requires the T to comply with HOA rules.