Thirdly, financing and potentially selling later on could be challenging again with the part of the plan being on a campground. 

This property offers spacious townhouse like setting floor plans offering one, two and three-bedrooms.

And yes, there is a risk that your rates would go up or they can drop you - but unfortunately, many insurers in that are may already be planning to exit the market or raise rates on everyone to make up for loses.One thing to note about a claim like this, insurance will usually pay for repairs to the damage caused by the problem, but not fixing the actual pipe that broke.

So this involves hiring an architect draw up plans ($1,000 - 3,000 if I had to guess).  

It’s exciting to hear about your plans to dive into this field, and Chicago is a fantastic market to explore once you move there.It sounds like you’re on the right track with your interest in House Hacking, Mid-Term Rentals, Short-Term Rentals, and the BRRRR strategy.

That could be your PM company if you plan to hire one. 

Share a clear business plan with numbers showing expected purchase, rehab costs, ARV, and rental income.

Projected sale: 950-990k Replacement property budget: 990k - 1.1M Plan: rent out the replacement home until meeting the requirements, then move into it while renting out a portion of the home via short-term rental 

The best thing you can do is plan that the first year will be on the lean side.

No one expects you to put money down when you tell people exactly what you are planning to do and how it works.Forget what everyone told you about how wholesaling is done.