I am happy to make some connections with some other Chicago investors as well!

I understand you don't need a lot of space, but you are paying someone else's mortgage.I would start with a fixer-upper investment, up to four units.

She can set up payments to be paid on the 1st of the month and no one is driving 24/7. 

New builds-broke even in the '08 market on two spec homes, built my own home from the ground up twelve years ago(400k in equity). 

.: Used to be able to ask for social security numbers on Applications.Who's stopping you?

I am seeking recommendations on how to network with investors and find those who may be interested in coming on as a joint venture/partner.

I'm sure it's a little more efficient in larger cities, but my market requires up to 60 days to get approval.Lower your expectations with Section 8 tenants.

Passive Activity Losses: Are there ways to offset my W-2 income with rental losses, or do I need to qualify as a real estate professional for that to work?

Joshua Tree is a bit of a tough market as there are a lot of STRs in the area.Be prepared that your first year might be a little thin as you are new and need to build up some reviews to get rolling.The interior is a bit of a toss up.

No qualifying and the ability to use your money to purchase something else?