My 13th hour cancellation was someone who had booked for 3 weeks and after a week announced that her plans had changed and she was leaving the following morning.

My plan was to purchase a lot and build a foundation, bring in a doublewide/manufactured house. have it placed on foundation and have a structural engineer reclassify it as fixed real estate. then, I would refinance. 

I’m starting off wanting to get into a primary residence that I plan to house hack and then figure out the next move into investment properties but that’s down the roadwith all that said, are there other ways that im not thinking of to 1.

You need to make a written plan with him to get this over the finish line, with cost estimates.

And don’t skip the due diligence—inspect everything and plan for unexpected costs.Take it one step at a time, and you’ll do great.

You Can Only Have 35 Non-Accredited InvestorsRule 506(b) allows an unlimited number of accredited investors but restricts you to only 35 non-accredited investors.However, there’s a catch:Non-accredited investors must be financially sophisticated.They must have enough experience to evaluate the investment risks.From the SEC:“Securities may not be sold to more than 35 non-accredited investors… [who] must meet the legal standard of having sufficient knowledge and experience in financial and business matters to be capable of evaluating the merits and risks of the prospective investment.”If you’re planning to include non-accredited investors, make sure they qualify—or you could be violating SEC rules.3.

Maintenance hasn’t been too bad so far, and I recently made the decision to sell my business, so now I’ll be living off my rental income.My question is: What should my plan be from here?

--> This is my plan.

This can be good because your realtor will be using them as a resource to help you plan your 1031.

.✅ Hands-On Experience – If you plan to grow your real estate portfolio, managing tenants yourself can teach you valuable lessons about leases, maintenance, and local rental laws.✅ More Control – You’ll personally handle tenant screening, rent collection, and property upkeep, ensuring everything is done to your standards.✅ Stronger Tenant Relationships – Being involved directly allows you to build rapport with your tenants, which can lead to better communication and longer leases.Cons of Self-Managing❌ Time-Consuming – Dealing with maintenance requests, late-night emergencies, and tenant disputes can quickly become a second job.❌ Legal Risks – Chicago has strict landlord-tenant laws.