@Kyle LipkoRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is expected to be higher, you may consider an umbrella insurance policy.

A standard 1031 exchange requires that the same entity selling the property also acquires the replacement property, which becomes challenging when proceeds are split between partners.Potential Strategy: "Drop and Swap"One approach is the "Drop and Swap" method:- Convert Ownership: Before the sale, the LLC distributes the property to the partners, converting joint ownership into individual tenants-in-common (TIC) interests.- Individual 1031 Exchanges: Each partner can then independently conduct a 1031 exchange with their share, deferring capital gains taxes by reinvesting in like-kind properties.Considerations:- Timing: The IRS may scrutinize transactions where the "drop" (distribution) and "swap" (exchange) occur in quick succession.

Quote from @Michael Smythe: @Jerry NoguerasRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

Bonus - the interest on the loan is tax deductible!

For your $2M property, a cost segregation study estimates $316K in first-year depreciation (compared to $28K with standard straight-line), potentially saving ~$117K in taxes at a 37% rate.

.✅ 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.

Like Dan, we have a standardized paint (white clay by Behr in eggshell, but SW will mix it NP) Thank you for the suggestions Marcus.

Tax Benefits: Rental property owners can deduct expenses like property taxes, insurance, maintenance, and depreciation, which could offset income.

My basic underwriting making some standard assumptions on HOA expenses, 20% down, 7% interest rate, 30 year mortgage, utilities, supplies, and maintenance costs shows a loss of about $22k per year if you are self managing.