Mortgage 15/1 arm at $3.375% with max 4% interest increase due 15 years from July 2015 (Aug 1, 2030).Current condo monthly maintenance fee : $1036 includes water, amenities (pool, tennis court, concierge, gym, sauna, community room with pool and ping pong, maintenance)Current monthly mortgage payment: $499 interest, $504 principal Monthly taxes and insurance: $459 monthly contents insurance: $38Past Assessments: $11k for building HVAC upgrades $8k for building updates and building reservescurrent market value $400k - $425kcurrent  monthly rental median: $3100-$3200monthly landlord insurance: $45I'm also trying to decide if I should rent or sell and invest elsewhere.Appreciate all insights.

That is a fairly complex exchange that will be difficult to execute.  

AI will be able to replace all repetitive labor jobs first and then more complex jobs. 

If that's the case, while I agree you should submit the claim to your title insurer and not the agent who issued the policy, I suspect the claim may denied as a matter occurring after the date of policy and therefore excluded from coverage.I handled a similar title claim and found courts had found that a tax lien as a result of a reassessment of the property became effective when assessed and was not retroactive. 

They can be used against you in court, even if you didn't do anything wrong. 

For house hacking your first house these things don't need to be overly complex, but you do need to think about them.

We filed to have them evicted and the court issued a writ last December.

But 2-4 units is Chicago is extremely complex with 100+ year old buildings, Chicago zoning, department of buildings with violations and inspections, plus the RLTO. 

We spent four years in a duplex, maintaining it in our rental portfolio as we transitioned to another house hack residence with an additional accessory dwelling unit-type house next door.Navigating the intricacies of FHA loans in competitive real estate markets can be daunting, given stringent home requirements and more complex processes.

Options may include traditional mortgages, private lenders, partnerships, or even self-directed IRAs.Calculate all potential costs including property acquisition, renovations, property management fees, taxes, and maintenance.Property Selection and Due Diligence:Use your local team to scout properties that match your investment criteria.Conduct thorough due diligence including property inspections, financial analysis, and reviewing rent comparables (rental rates in the area).Make Offers and Negotiate:Submit offers based on your research and due diligence.Negotiate terms that are favorable to your investment goals, taking into account potential repairs or improvements needed.Close the Deal:Once your offer is accepted, work with your local team to complete all necessary paperwork and close the transaction.Ensure all legal aspects are handled properly, including title searches and property inspections.Manage Property Remotely:Hire a reputable property management company to handle day-to-day operations such as tenant screenings, rent collection, maintenance, and emergency repairs.Establish clear communication channels and expectations with your property manager.Monitor and Adjust:Regularly review your investment performance and financial metrics (cash flow, occupancy rates, expenses).Stay informed about market trends and adjust your strategy as needed to optimize returns or mitigate risks.Long-Term Strategy and Growth:Evaluate opportunities for portfolio expansion or diversification in the same or different markets.Continuously educate yourself on real estate investing best practices and market dynamics to make informed decisions.By following these steps diligently and leveraging local expertise, you can effectively navigate the complexities of out-of-state real estate investing and build a successful portfolio over time.