When considering a vacation rental property, it’s essential to have a backup plan and understand the numbers for annual leasing.

Any advice would be appreciated.I would first talk to a real estate attorney or a foreclosure attorney to make sure that the way you plan to do things passes muster.

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 and UpkeepRegular Inspections: Schedule periodic property inspections to address maintenance issues.Emergency Repairs: Have a plan in place for unexpected maintenance needs.Furnishing the Property: Budget for necessary furnishings and appliances.7.

I’m at the very beginning of my REI journey and I would love some guidance on how I can best optimize my planning, research and saving phase (which I’m dedicating 2025 to).

If youre saying condos are trading at $220 a square foot....Id be planning on a value of $110 per square foot on a co-op.

I’m just currently in the planning phase to see what the best path going forward is.

Would love to hear your plans. 

That’s why the successful wholesalers and flippers I know spend $10,000 and more MONTHLY on marketing.  2.

.✅ 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.