What if they have collections or judgments?

In addition you can use it to collect initial security deposits or to bill the tenant for addition items such as billed back utilities, damages, etc.

Theoretically, I should be able to collect the funds from the deal, should my family member decide to go through with the deal.

In the meantime, you're paying interest on the $448k.If you did your 3rd option, the seller is essentially becoming a Limited Partner in the deal, which I wouldn't advise unless the seller is very sophisticated.

They have to prove to any relatives and "legally" interested parties, (court, relative, creditors, etc) that all money was collected and all debts were paid.  

Just started using https://www.turbotenant.com/ it gives you a focal point to house documents, gives you a credit report and some other things but it's still your decision to make with the collected information. 

I already have a Stessa account which can be connected with a bank account and has the benefits of collecting rent and keeping track of documents, receipts and transactions.

If the property was in Hartford proper, we would tell you no to management since the tenant base is much harder, it is harder to get rent collected on time.  

By partnering with like-minded investors, pooling resources, and leveraging collective expertise, I unlocked exponential growth. 

Then look at places where you can buy those properties, and last investigate with HUD what is the section 8 rental in those areas.In that way, you will collect a lot of knowledge in the process.