The question is: Do I let her rent longer, continuing to collect, then renovate before the next renters' cycle (around March/April or later)?

But you're buying in a high appreciating area so it may be worth having renters water down your principle while you appreciate.

Here’s a breakdown to help you navigate your first deal, incorporating advanced strategies, including 1031 exchanges, to attract a broader range of investors.Neighborhood Recommendations: Chicago offers a diverse range of neighborhoods for different investment goals:Wicker Park & West Town: These areas are known for their strong rental demand among young professionals and offer good potential for cash flow.Lake View: Ideal for attracting tenants who want to be close to downtown while enjoying local amenities.The Loop: A prime location for high-income renters, making it an attractive option if you’re planning to house hack and generate a steady stream of rental income.Property Types: Opt for properties that align with your investment goals.

Have you surveyed the EV ownership rates among the renters in your MTR area?

I have 4 properties in Ft.Myers and was spared this time, but the anxiety is real.I would have your tenants contact their renters insurance if they haven't already.

So I would likely have to place this responsibility with the renter. 

How will you do this and ensure you don't accidentally bring in another bad renter?

so you've eliminated a HUGE pool of renters. 

Like I said this is our first property and it’s a special case since I use the portion of the house (in the bedroom) as my office and we rent out technically 3 bedrooms 2 baths to renters.

You could also offer a gift card to a local gym to keep things fresh for health-conscious renters.