What I assess is whether they are willing and able to continue paying the rent, generally speaking if they have been paying for the last 2 - 3 years that is not going to suddenly change.There is a bedding in period with repairs.

In 2017 we had a special assessment to have our decks repaired due to faulty construction and leakage issues with the commercial unit which spans all 5 residential units.

Double / Triple check the #'s and HOA fees make sure your realtor is in the know regarding any assessments etc. 

And then, I actually called the collection agency and left a dozen messages for them to please call me so I could pay off the collection. 

In order to accurately assess why this bid is so high there is a lot of info that is needed that is not provided, but in general when there is a lot of wallpaper removal involved contractors will often account for worst case when it comes to the amount of time it is going to take them to remove it. 

you can get a home assessment from Georgia power below and qualify for rebates from the utility for things to include insulation and home sealing along with the asessment fee:http://residential.georgiapower.com/products-progr...There is also a free home energy audit available that might be worth considering if you don't want to shell out for an more detailed  assessment:http://residential.georgiapower.com/products-progr...Start with that and see what they recommend.

If you have any good referrals of attorneys/brokers who specialize in assessing the overall risk and recommending  proper insurance to mitigate those risks, please let me know. 

On his latest purchase he didn't do his due diligence and found out (1) month after closing that there is an assessment due in the upcoming year.

My broker manages 400 houses and I clear more managing a dozen properties (that I own) than he does.

No need to have dozens of accounts.