Keep in mind, every PMC software has limitations, but you should be able to get at least 80-90% of what you want.

I currently work as an embedded software engineer.

Buildium is a property management software and quickbooks is accounting software. 

I want to make sure Im prepared with the correct documentation to rent out my condo and would appreciate all opinions if im missing anything: - I have the rental application- I have my rental property agreement that I will have the renter sign and make copies of and provide them a copy.- I have the statement of condition that I will have the renter sign and make copies of and provide them a copy.- I will have them provide a copy of their tenants insurance for my records. - Will provide receipt for first and last months rent.- Im thinking of not charging security deposit because of all the strict MA laws and just using the last months rent as a sort of security deposit, thoughts?

This can enhance your application and improve your chances of securing a loan.

In our24 years of experience, managing almost 100 S8 leases currently, the average S8 tenant has a FICO under 580, numerous collections from utility & cell phone companies, doesn't want to pay a security deposit, much less an application fee and claims they don't know how to fill out their S8 paperwork despite being in the program for several years - hint: they want YOU to do it for them.Most, not all, are eligible for government assistance due to a funeral-march of bad choices.REALITY: you are trust trading one set of problems for another.You can succeed with S8, but you need to understand the challenges and plan accordingly.

I utilize professional Autocad software.

If you have an emergency contact or other info on their application you can try that info to contact  them. 

The various "what-if" on neglect, just like with a tenant it's violation of contract terms and you take the applicable legal actions. 

Is it only applicable if I then try to rent out a basement that has been converted?