For anyone that has hired an employee to do your own construction work (1099 or regular) how do you handle contractor liability insurance?

They are almost always grandfathered in as they were compliant with building standards when they were constructed.

I run a construction group that mainly does high end stuff on the east side, Cle heights and Shaker heights.

Really old buildings back in the day did not have as many checks and balances to get approval from city or county inspectors even if they had them at all.

I've built before so I can handle the construction.

I would call it a red flag if they resist giving you everything you request for your DD document list quite quickly, their speed and thoroughness in response to that shows their willingness to sell imho.When you schedule your inspection you want all your professionals there at the same time to go through a single time, contractor, inspector, and any specialists you think you might need like roofer, engineer, etc.Also don’t feel pressured to make your DD and inspection time as limited as is common in SFR, give yourself 2-3 months at least, again, from when they deliver the docs you request.Besides financial DD you want to do physical DD not just on the property via inspections but visiting the area during day and night, weekdays and weekends, to ensure you have a feel for everything that’s happening at different times all the way around the block.

im looking to have a roof looked at a little closer than a home inspector would.

New construction or resale. 

Is there a mechanism to 1031 the commercial building I own into the construction of a new duplex on land I own?

im looking to have a roof looked at a little closer than a home inspector would.