Quote from @Cliff James: missing Chimney flue liner and missing rain cap; significnt shingle granule loss, missing drip edge flashing, vent pipe flashing missing, cabinet handle missing, siding pieces missing, gutter down spot missing, Old wood/aluminum windows, prior water penetration observed (Efflorescense),If the roof repairs makes you feel uncomfortable, request an additional inspection by a contractor or roofer (assuming you checked "Any additional inspections deemed necessary" in your purchase contract).

I have a few select trades that I swear by, my Electrician, HVAC, Roofer, Plumber, foundation crew, and select and sub out the rest as needed.

The house needs a roof and the existing roof is very old asphalt over cedar shake so according to the roofers they need to completely remove everything down to the rafters and install 5/8th inch plywood then reroof from there (one estimate so far came in at $31k for that).  

So, they’re a real good alternative to consider; however, in this era of low cap rates these loans may not result in any cash flow (expenses always seem to be higher - the a/c unit needs to be replaced; the small roof leak reveals that the last roofer neglected to install underlay; etc - tenant do more damage than the security deposit and replacement tenants with decent credit take longer to find).  

They each have Roth-IRAs.As we get older rents will increase, mortgages will start to go away one by one, and we will have access to better cash-flows.No need to save for retirement, as we essentially are retired at this point, and living off the rental income without having to touch the retirement accounts, as was the point of this post... and we maxed out IRAs and 401k early on, so those have enough basis in them that they don't really need any future contributions to balloon into awesome assets by traditional retirement age.I don't necessarily want to Die with Zero... but to keep the Golden Handcuffs of my W2 on till I reach $10M sounds like a very unnecessary waste of my life based on fear.I appreciate your point of view, and I know there are risks involved, just yesterday I met with a roofer to put a new roof on one of my units, but I've checked my historic repair costs, future potential capex projects, and done my best due diligence to move forward towards a life of freedom on my terms.Here is a closer look at our personal finances if anyone is curious, also we have access to $300k in HELOCs that are unused:$285 per year for kids activities for 5 kids?

I am sure there are exceptions but most of the reports we see all say "Recommend that you contact a licensed electrician / plumber / HVAC / roofer for further inspection" and if you read the fine print, they typically say that they are not responsible for any missed issues. 

I had a roofer (he works for a roofing company so knows what he is doing) fix the roof, put back the carport and the porch roof.

My current flip was bought from a wholesaler in a partnership with a builder friend of ours who has his own salaried framers, roofers, plumbers and electricians.  

You think the roofers and lawn care guys around me hire Mexicans because they like them?

I was talking to one roofer and he wants 16K for a metal roof to put over shingles.