The fund management and LP reporting experience can be adequately managed through a good fund administrator.

https://www.toledoblade.com/local/city/2020/06/26/kapszukiewicz-administration-delays-lead-safe-housing-enforcement-citing-coronavirus/stories/20200626079The latest and greatest on the Toledo Lead Ordinance.

The "administrative redemption period" continues for three years after the date of the tax sale.

I would say paper work, accounting, reports and administrative tasks are the easier part as there are software programs you can use. 

The company I worked for ended up having to sell itself to stay afloat, at which point I began picking up a few more certifications (I'm a network/systems administrator).

Boots don't give advice or facilitate the transaction to either side, they only perform an administrative support role.

Some times HELOCs have a little bit more administrative oversight depending on the Mortgagee so I would recommend disclosing the LC/CFD.  

The zoning administrator at the township says the only way to determine whether it is an illegal split is to get a legal opinion, which they won’t spend the money for until the property is sold.

The cost and complexity of administration as compared to just having separate standalone LLC's is generally not much different. 

Section 25 of the "standard" SC contract says "Thebenefits and obligations shall inure to and bind the parties hereto and their heirs, assigns,successors, executors, or administrators."