Additionally, if he’s legally and financially tied to the property, it might limit his flexibility if he wants to make major life changes, like moving or starting his own investment ventures.Ultimately, the decision depends on how involved you want him to be in the financial side of the property and how much risk he’s willing to take. 

I'm reaching deep into my psychic thoughts… I see it… A majority of people who respond to this post will be real estate brokers… I can see it!

The majority will most likely want an equity position in the deal, and since wouldn't have an active role I'd be getting into a syndication rather than just a JV.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Most hosts in Chicago just pocket the full funds from direct booking, you would be in the very very small majority if actually paid city taxes on it.

Their insurance has asked me to return the month's payment for the remaining days of their rental (Unfortunately, I did not have a cancellation agreement).I am unsure how to handle this situation, especially since I couldn't fill the majority of the rental dates and had to offer discounts for the days I did manage to book.

Hot tubs can be a major revenue booster for STRs, especially in colder climates or vacation destinations.

The lease has a clause where if full rent is not paid by the 10th of month, I am allowed to evict as he broke the lease agreement.I am willing to work with him but overall I would like him to move out as I seen major signs of depression and hoarding behavior but I don't want him to turn into a squatter.

The moment you buy an investment property, start a side hustle, or even experience a major life event (marriage, kids, inheritance, etc.), taxes get more complicated.

Purchase price $525K, appraised for $760k (no major nor significant Reno was had).