Ideally I'd like to find a LINE of credit of some sort.

HI Michael,the answer to all 3 is yes. since the properties are so close, one or the other would have to be a an Investment property. since this is your plan of action underwriting should have no issues as there is no means of mortgage fraud with what you plan to do. one thing you will want to keep in mind when qualifying for the new home is debt to income ratios, and having a renter with a signed lease agreement for your current primary lined up will off set the debt ratio helping you qualify with no troubles.let me know if you have anymore questions or want to speak privately! 

I would like to keep using a cheap, larger format tile (so that we minimize grout lines) with dark colored grout, but need some fresh ideas to modernize it a bit. 

I just wanted to make sure to be able to line up my own financing in case he says no.At this point in time, I'm not really looking to partner with anyone because I don't want to have any pressures on me regarding expectations with this lot.

It's a 4 bed, 2 bath house that is just large enough to house-hack.

If you are only doing minor work, you might be able to get the subs to pull their own permits, but this kind of defeat the purpose of being the acting GC as the sub will probably charge you for getting the permits.There is a thin line between being the "GC" and being a program manager.

As long as you are in same line of work  you  will be fine. 

Hi -  We are under contract on our first buy and hold that we have been able to find that has decent numbers...Would appreciate any reaction or input anyone has to this deal...good/bad/bad assumptions etc.Location - 63rd and Halsted (very close to the new whole foods developmentProperty - Grey stone with 2 units (3 bed/1 bath) unfinished basement with laundy and 2 car garage.  

Any recommendations for an insurance broker to help me get across the finish line and properly manage my risk?

If you're paying much over market price, there's a problem in how the company does business up the line - they should be making money on the purchase+rehab/ sale price spread because they can execute rehabs cheaply and efficiently due to economies of scale.