For example the license should not only have a cost but also require at least some compliance training targeting some of the most common issues/complaints.

Quote from @Abhijit Roy choudhury: Financial Crime enforcement Network, requires reporting of Beneficial Ownership Information filing by 01/01/2025.Does this apply to us, Rental LLC owners.

If you control how they perform tasks, set their hours, or provide tools, they should likely be a W-2 employee, requiring you to withhold taxes and comply with payroll regulations.

Common fees will include a set-up fee, a leasing fee for each turnover or a lease renewal fee, marking up maintenance, retaining late fees, and more.

You state there's a lot of deferred maintenance, then state it is a remarkably well maintained property.

Often it's a really easy fix or operator error that does not require a pro.

We purchased 133.7 acres January 20th of 2024, we then proceeded to subdivide 4 building lots, ( two 10 acre lots,  and two 2 acre lots)  which included costs associated with septic testing,  survey & subdivision, and property maintenence required to market the building lots.

You'll need more capital and most will require a personal guarantee and personal financial backing. 

With Chicago's new Express Permit Program, it's a bit easier to get permits for work that would have previously required architectural drawings. 

2) Maintenance Reserves: So many factors here to consider!