@Derek Harville If your grandmother gifts you the trailer, you inherit her original cost basis, meaning if you sell it later, capital gains tax could apply.

If a property is for sale but currently has tenants in it, but the buyer is buying for their primary residence, do eviction laws still apply? 

In all markets in fact, this applies. 

Given that I'm not positioned to buy just yet, and simply running the numbers, is there a rule of thumb for estimating insurance costs that would make sense in Cook County?

If you have a rule, enforce it. 

Then, if or when you decide to sell, you’ll have valuable insights to apply as you roll those proceeds into your next investment property.

Learning how to use the correct tools and materials for a job, YouTube videos and even ChatGPT will help you get through 80% of the problems you will run into.My rule was I would not mess with HVAC, plumbing and electrical Or if it would take more than a few hours. 

If more than one person applies together, then we combine their scores for a group average.

This convenience and leverage can justify the higher cost of these loans.Personally, I prefer using a HELOC because I only have to apply once and can then tackle one or two projects at a time.

If so, shifting that to the tenants at the time of lease renewal is another great way to decrease her overall debt service.This has already been ruled to be against the substantial change of lease terms.