Focus on connecting with the ones who add the most value and ask for the least from you.

A landlord policy can be a commercial policy or a personal lines policy.It's the same as asking if you should buy a single family rental or a 1 unit building.Focus on the coverages and disregard the name of the policy.

It helps to make connections with your local flooring, tile, kitchen design studios depending on how high end you want to make your flip depending if it is in a HCOL neighborhood.

It very well could become a large enough investment to be worthwhile, also solving for "unexpected emergencies ", for the most part and would an easy self management situation if you were to live onsite in one of your connected townhomes.

I always remember that rockstars know rockstars, so find someone who is a mover and shaker - likely a meetup host - and then ask them who they know.The people doing 100 flips are super busy, so I've also found the best person to find is someone who is a step or two ahead of me...so maybe for you, that is someone doing 2-3 flips a year. 

I like the strategy of having a job with guaranteed income and taking advantage of owner occupied financing to purchase a house hack, staying connected with the REI community in the area, and scaling up from there.

I was hoping to connect will someone with some event venue experience.

If you need more to do the rehab, perhaps instead of partnering, you could get your former boss to do a personal loan. 

There are some great tools out there always, but get connected and network as much as possible.

If you’d like, I’m happy to connect you with professionals in Chicago who specialize in this.Best,Jarret