As part of your assessment, consider taking to a tax expert regarding deductions.

I want to have a professional come out and give me their assessment.  

They let their buildings creep into major water damage over the years and then struggled to pass a special assessment back in 2016. 

A more important assessment from you post is why are you not doing your own PM.  

-(borrower) will have 45 days from the day the money is received to repay the loan & interest total of $8,250 to (loaner)-The money will be used for (borrower)s investment property, at (address) for roofing, staging, lender dues, and materials/supplies-If (borrower) is not able to pay the loan back within 45 days, an additional $500 penalty will be assessed for every 15 additional days it takes to repay the loan in full.

Since in residential investments, the rental payments is relatively easy to assess (people pay rent before they pay medical bills), it's a product that would have a high collection rate and therefore the interest rate can be somewhere between hard money lending and mezz loan rates; all of this without the hassle of a lengthy process and with no resource on the property (just on the person or a direct integration with the rent collection/settings up a lockbox for collecting rents and dispersing them to the owner bank account minus the monthly interest payments).

I know the HOA regularly sends out notices that fines will be assessed if an owner is caught illegally renting their unit. 

Trying to figure out if I, as a buyer, am to pay this $200 "initial assessment" to the HOA? 

Then do an honest assessment of your knowledge, skills, passions, and abilities.

With this in mind, I understand there is no 'due diligence' period and therefore an assessment of what work (if any) a potential property may require, needs to be determined quickly; ideally on the initial walk through of a property (in order to get it under contract quicker).