I don't know which nearby state you're considering (PA is probably the most attractive) but local municipalities will sometimes enforce extra red tape and/or protections for tenants beyond the state-norm.

If it concerns you that much, adjust the purchase price to take into account this added risk. 

This is from the BP rental calculator and is exactly what I'm wanting to see, just with extra payments each month. 

If you’re leaning toward adding more units sooner rather than later, consulting with a zoning attorney or architect could give you a clearer path forward!

One reason was the condo management company wasn't doing a great job and there were always extra levies. 

I'm currently renovating my rear unit and it has the perfect layout to split into 2 units by adding a wall and an additional front door.

If you want to buy your first property ASAP, house hacking (duplex, triplex, or renting extra rooms) is one of the best ways to start with a low down payment while learning property management.

I got swayed by his pitch, not sure how I got added to his presentations.

My first ad budget was $295.00 credit I got from my local news paper. 

Adding the ex to the title could trigger gift tax implications, so keeping it simple is best.