Absolutely looking at other options (including direct booking) because want to keep learning, improving.

You might want to consider other options, like teaming up with a reliable friend or family member, to navigate this situation.Getting advice from experienced professionals in the real estate industry can offer valuable perspectives and assistance in dealing with legal and ethical issues.

Technological advancements are reshaping the real estate industry for investors in various ways:Data Analytics: Advanced tools offer insights into market trends and investment opportunities, aiding informed decision-making and risk assessment.Virtual Reality (VR) and Augmented Reality (AR): Remote property exploration with virtual tours saves time and resources, attracting potential buyers or tenants and expediting transactions.Blockchain: Secure transactions via smart contracts reduce intermediaries, costs, and fraud risks in property dealings.Online Platforms and Marketplaces: Digital platforms broaden access to properties, investment options, and real-time market data, enhancing efficiency and transparency.Artificial Intelligence (AI): AI algorithms predict market trends, identify investment opportunities, and personalize recommendations based on investor preferences.Internet of Things (IoT): IoT devices provide real-time data on property performance, enabling cost reduction, efficiency improvements, and better tenant satisfaction.Crowdfunding Platforms: Real estate crowdfunding democratizes investment access, allowing smaller investors to participate in projects previously out of reach.In summary, embracing these innovations enhances efficiency, transparency, and accessibility in real estate investment, enabling investors to capitalize on emerging opportunities and stay competitive in the market.Thanks!

Who knows.Another option would be to buy a small parcel and slowly build a house with/for him and pull owner permits.Am I nuts?

You should have this lined up and understand the options before you commit yourself to anything Especially if you are using hard money or any other then your own cash.

I think the easiest way to find the right partner is to find one that you are aligned with as far as investing in rental properties.The other option would be to keep flipping properties until you get enough money for a down payment on a rental.Another option would be to look for a BRRRR (buy, rehab, rent, refi, repeat) because then your friend could still bring money to the table and you could pay them back their portion plus interest and then you keep the rental property.What area of Chicago did you do your flip in?

Will consider going that option. 

Let me know if you'd like more details on this option. 

5) Is one month rent security deposit enough nowadays?

You might get quicker answers for there by reviewing some of the best STR options in your area on Airbnb and then finding the hosts or co-hosts offline to ask questions.