Some of NJ's laws are worse than NYC or Cali.Yes, NJ laws suck. 

Realistically im probably at least a couple years away.

Couple is splitting up and one is wanting to stay. 

It's usually better to earn $200 less a month for one year than to sit vacant for two months, particularly in the winter.Consider a bigger drop for a 6-month lease to get through winter, then increase rent or find a new renter in the spring when competition is hotter.

If you are single or a couple on the same page about house hacking, look for uneven multis.

I have a couple questions —1.

We have over 10,000 landlords in Milwaukee and at least a couple thousand active investors at any point in time.6.)

No one will watch our money more carefully than us, and have usually had some sort of arrangement (or try to) similar to what you've proposed. 

You'll probably get better service approaching it that way than hiring a professional manager anyway.  

I was told that a ground-floor condo are better than a second floor condo ( If there's no elevator and Stairs are present).