Luckily, I did not include this unit in my underwriting when purchasing, so the survival of this property is not contingent on this situation.Continuing to optimize for management of the building when I move out, like moving everyone to online rent payments or adding remote accessible security cameras.Exploring opportunities to expand my portfolio—I've begun my hunt for my next 3 to 4-unit building to house hack, ideally in Lake View, North Center, or Ravenswood.This year taught me that real estate investing isn’t easy, but it’s undoubtedly worth it.

He isn't rich enough to have a body guard and a security professional.

It seems like offering this as a separate package once you secured the booking is a good idea. 

In the lease it states that a security deposit of 1 months rent was collected. 

Look for undervalued properties.Network: Connect with local real estate agents, contractors, and other investors for insights and deals.Analyze Properties: Use the 1% rule to evaluate potential properties (monthly rent should be at least 1% of the total investment).Secure Financing: Explore different financing options like conventional loans, hard money loans, or private lenders.As for timing, if you can handle the extra responsibility, starting now could give you a head start.

Consider all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

The lender lent based on them being one thing which secures the debt.

Landlords can enter a tenant's property for a variety of reasons, including: Making repairs or replacements Responding to a tenant's request Removing unauthorized window coverings Preventing waste of utilities Changing filters, testing, or replacing smoke detector batteries Inspections Helping with an emergency inside the unit Posting a notice of eviction"Research your state laws because some of your comments indicate a lack of understanding of the landlord/tenant laws where you are operating (like threatening the tenants to keep the security deposit if they don't respond to you, I doubt that is actually a valid reason to keep their deposit, or evicting for late payments, or charging the tenants for your warranty repairs because you missed your 11 month inspection window which was your responsibility, and it looks like your lease says you can charge up to 18% interest for unpaid fees, is that actually legal?).

We have not been able to secure financing and had conversations about it.

If you're living in it now, you'll probably be required to have a signed lease in place as well as proof that first month's rent/security deposit were collected in order to get a DSCR loan (they're business purpose loans and don't allow owner occupancy).