I redid the roof… it’s multicolored… used up shingles I had laying around… but still a new roof.Trying to decide if I should sell it.

Find a reputable roofing company-look at online reviews and find one that has been in business for a while...ideally local company.Inspect the roof-are shingles curling? 

My lawn company cleans but they don't always do the roof so it sits on the shingles, which can cause issues not only to the shingles but eventually the decking and interior attic area ( I presume so just like standing water on carpet will do damage) - so now I'm making sure the lawn guys look up on the roof to make sure it stays clean.So this "moisture" that was detected or presence is being taken care of to ensure there is no escape into any part of the house if that is likely.The test they did though showed no evidence of anything in the home.The tenants were presented with a settlement or buy out or what ever the language of the day is for them to leave and guess what......they had their own air quality test performed and they paid for it and that company also said there was no mold in the home.My PMs did an inspection and they are changing the air filter and keeping the home very clean.So now they are staying presumably until the lease end.Geez!

All:I have ~30 properties/50 units and seem to have to replace shingles on 2-3 roofs every year, not to mention the new roofs I have to put on properties that I acquire. 

I've been considering several approaches for re-entry, with the brokers license and the ability to hang out my own shingle in the center.Brokers and PM's are already regulated as to the handling of client funds through trust accounts and making sure those funds are segregated and accounted for separately, so no desire to comingle or involve "his own account" with SD money in any way, and I have no questions about how to handle the bank/accounting aspects to support that.In my mind, (don't start), nothing I had hoped I might do, would infringe on an otherwise arms length transaction, or impact my SD account beyond the wisdom of my own investment choices.

Also will need shingle repairs and painting some time in the next 5 years since in HOA.  

For example a roof might have a 25 year shingle but with monitoring and minor repairs can easily last 30-35, maybe even 40 years!

Get your PE and have the outlook to be self employed (hang out a shingle), along with your real estate ambitions. 

If that is a shake roof, replacing it will also need all new sheeting underneath the new composite shingles, since there was none with the old shake roofs. 

Considering that few tenants climb up on the roof and tear off the shingles, or take sledgehammers to the units, you would still be looking at a reasonable profit over time if all of your catastrophe came true.