To stay secure, I’d recommend saving 3-6 months of mortgage payments, budgeting for repairs, and possibly investing in a home warranty.

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.

Agree with @Jeff Pollack on having the guts to leave the security of a JOB.

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.

He is securing expensive debt, not debt through a bank, isn't putting any capital into the deal and structuring the equity investment in a highly risky manner without any upside offered to the investor.

Depending on the application, first, last, security, and another month or two.

You have engaged and paid securities attorney and are compliant with Reg D offering 

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.

What ********.1) spent $250 for 60 days notice of termination to tenant back in July (stating owner will move back in October and take house off the rental market; within the laws and does not violate covid non-payment); also tenant rekeyed house back in April, in direction violation of lease agreement2) October comes and tenant still there, providing statement of covid hardship and states she doesn't have the financial means to move and will be staying put3) spent $1600 to eviction attorney to proceed with the serving in October4) tenant's attorney replied back on 12/1/2020 stating to give them a 60 day extension so they will be out end of January (to which I agree to)4) finally got a case number (trial is set for Monday, December 21) which happened yesterday; but now they are continuing to bull **** (the nerve of them to ask for one month security deposit back and I should forgive them of all debt and not pursue small claims court if they move out by Feb 1)5) I told my attorney ********, no way are they getting anything back from me and I will pursue small claims court for all back-rent owed plus property damage plus all legal fees6) so the trial continues and will re-convene back on 1/21/2020What a load of crap.

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