I will not, under any circumstances, send a copy of the borrower's financials documents to a seller/agent. 

This is where a lot of people make mistakes and then keep those mistakes going until they decide to outsource it.Also, Tax Accountants can create Profit and Loss Statements but that isn't their specialty and they aren't focused on keeping your financials in order.

The biggest issue I’ve faced is unreliable syncing with financial institutions.

I could see a value-play here for monthly financial reporting, if not handled directly through PM systems.

DO NOT invest with Chris Walters or Jim Thorpe, they are repeated and known scammers who have been issued fines by the WA State Department of Financial Institutions and are currently under investigation. 

@Jacob NevarezRecommend you figure out the property Class you want to invest in.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a Class A property in Class D area, what quality of tenant will you get?

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

The tenant claims he's under financial stress due to being out of work after an injury and is struggling to get the funds together for the funeral services.

But, again, if you friends  in Indy know a thing or two about investing and can partner with you, where you both have a financial stake and they get "more" of the pie relative to their equity contribution in order to oversee the success, that would be the ideal scenario in my book.As for broadly in markets, both are considered pretty good.  

Can I even be financially independent in this situation?