I read Chad Carson's Small and Mighty Real Estate Investing and I think my path is most aligned with what he calls the "live and fix" method.

Are employers moving in, is the population growing, is the average household income high, does it have good market fundamentals?

You will need to read them and do some math, but this would allow you to calculate costs and evenly allocate them if they go 50/50.

Also, I would definitely read that book by David Greene!

After reading through nyc.govs lengthy explanation on M1 zoning laws, I am still trying to figure out if we can do this or not.

Yes, you read that right, the American system was designed to best facilitate FAILURE not success. because when there is freedom to FAIL, it comes from consumers ability to choose, choose who is worth it, who isnt, and the poor performers fail and the good performers are rewarded. 

Then you can read a more in-depth book like The Book On Rental Property Investing by Brandon Turner or The Unofficial Guide to Real Estate Investing by Spencer Strauss.2.

Do they have the necessary resources to stay on top of all the tax issues such as 1031 exchanges, 754 Step-Ups, etc.Feel free to send me a private message if you have any questions here.A couple articles you can read that will be helpful:https://www.biggerpockets.com/forums/51/topics/1206189-cost-...https://www.biggerpockets.com/forums/51/topics/1204912-how-t...

First, I have read that many people are not obtaining permits.

.- The numbers may have an impact on your decision.You may also want to read your condo's Home Owners Association Master Deed & Bylaws to make sure there are no restrictions on any type of rentals. - Many HOAs have LTR restrictions and some now have implemented STR restrictions.Also, hopefully you've updated the home insurance policy of your current STR rental from a homeowner's policy to a landlord policy.