We're closing next week on an event venue with 10 lodging units on-site. 

This is what scammers and con artists do.

I could use some help from investors in IL... how do you set up a sub to there??

Market Analysis is one of the biggest things I do. 

You can definitely do it.

Or you could end up spending more time than just doing the work yourself. 

When I floated the idea of buying it from them myself, they said they were open to it if that's what I wanted to do and gave me time to think about it.

If you do not qualify, you would then look into if you would qualify with renting your departing residence. 75% of the lease will be used to offset that departing residence mortgage. as you mentioned the timing of renting the place can absolutely be tricky so you would hope you do not have to do this.Finally, and I guess would be sorta of a trick, but we do bridge loans on occasion in this case IF you can qualify once you get the property rented at market value even if debt to income ratio is too high before it is rented.

I am doing three right now.

Which I also have experience doing.