Using such cheap “handymen” is a good way to end up like the chic in Shameless when the unlicensed roofer’s “employee” fell off her roof and sued the property owner. 

I am negotiating with a few roofers, and hope to make a deal. 

So I recommend you plan on that goal in your decision.To manage your own properties you need to build your own mini-property management company...who is your electrician, plumber, roofer, who does your evictions, attorney to advise on those split-second decisions, how are you collecting rent, preparing leases, showing units to rent, the list goes on!

I dont think the professional roofer was professional when he asked you where is the man of the house.

Get a HVAC guy to inspect hvac, plumber to inspect plumbing, roofer to inspect roofing etc.AND IF YOURE A GUY - GET YOUR WIFE"S OPINION!

Not all of them do.Develop your network of lenders and repair people such has plumbers, HVAC, electricians, and roofers.  

Our roofers, they are the ones who really work!  

.- Find all trades, negotiate price & timelines (Roofer, Painter, plumbers, electricians, etc)- Find a Architect, negotiate price- Find an engineering company- shop price - Find a survey company negative price - Find good realtor that works with investors.

The roofer patched what needed to get patched for $300. 

(I have had tenants turn the AC off when they move out or the heat in winter)- We require they have someone check on the property if they leave it for more than 5 days (This is to make sure there are no water leaks or HVAC issues that lead to problems while they are gone)- No businesses can be run from the property (to prevent day care, laundry services, gambling, drugs or who knows what)- We specify yard care includes week spraying and cleaning up sticks less than 1" in diameter (otherwise tenants think yard care is mowing only)- We state that tenants utilities can be used for routine maintenance or repairs (I once had a tenant complain the roofers were using his power for their compressors)- We have a whole section on mold stating that mold is naturally occurring and results from excess moisture.