If property is occupied they can stay 90 days since you give them 90 days notice, before you can start eviction process ( in DuPage county takes usually 6 to 8 weeks ) You can try pay them to leave but usually doesn't work since they know how long they can stay for free.

Though it might be naive, I was thinking of a buy and renovate project that would cost between 150k and 200K.Any recommendations and/or resources towards this goal would be greatly appreciated.Hi Damion I have a long time friend that has been doing fix and flips in Philly for the last decade..he’s certainly done very well for himself. 

Converting your single-family home into a rental property involves several considerations to protect yourself and ensure smooth operations: Establish an LLC:Liability Protection: Holding the rental property in an LLC can protect your personal assets from potential lawsuits related to the property.Tax Benefits: An LLC can offer tax advantages, such as pass-through taxation, where rental income is taxed at your individual income tax rate.Insurance:Landlord Insurance: Ensures coverage for property damage, liability claims, and loss of rental income.Umbrella Policy: Provides additional liability coverage beyond your landlord insurance, offering extra protection.Deductions:Mortgage Interest and Property Taxes: Continue to deduct these expenses.Depreciation: Depreciate the cost of the property over 27.5 years, excluding the land value.Maintenance and Repairs: Deduct costs related to maintaining the property.Property Management Fees: Deduct fees paid to the property manager.Filing Taxes:Schedule E: Report rental income and expenses on Schedule E of your tax return.Separate Accounts: Maintain separate bank accounts for rental income and expenses to simplify bookkeeping.Lease Agreement:Solid Lease Terms: Ensure your lease agreement is thorough, covering rent amount, due date, late fees, maintenance responsibilities, and eviction terms.Legal Review: Have the lease agreement reviewed by a real estate attorney to ensure compliance with local laws.Tenant Screening:Background Checks: Perform credit, criminal, and eviction history checks on prospective tenants.References: Contact previous landlords and employers for references.Property Management:Regular Inspections: Schedule regular property inspections to ensure it's being maintained properly.Maintenance Fund: Set aside a reserve fund for unexpected repairs and maintenance.Moving Out of State:Communication: Maintain open communication with your property manager.

I think the medium term rental strategy would work well here.

You get your money without the tax hit at the moment and hopefully continue to profit off them,   If the objective is long term passive income, it doesn’t make sense to sell them… it moves you away from your goal post.  

Most lenders do not like these lower property values because they are too risky of an asset class, little return in interest and fees, and long term financing will be an issue as well.

Just depends on your long term goals. 

I’m also in San Antonio and I am a property manager for short and mid-term rentals.

As long as they pay all their bills and have been according to their credit check I'd rent to those people every day.

So, I came accross a short term rental market analysis report for the city of Fresno, and found a really interesting chart representing the seasonality of the short term rentals.