. $50 per bedroom, so a 4-bedroom house will cost you about $150~200consumables - bathroom supplies, kitchen supplies, beverage supplies: $20~30 per week, depending on how much you providewear and tear - towels, linen, kitchen utensils, some furniture: $1000~2000 per yearRepairs/replacement for things that guests break or steal:  $1000~2000 per yearAlso, if your personal use is less than 14 days a year, the entire property's expense is deductible against STR income, but if you use more than 14 days, then you will have to calculate the proportion of how many days it's rented out vs how many days you or your family uses. 

I personally think you can successfully market both your property management (PM) and buy/sell real estate services under one brand if you position them correctly.

Yea this is a long-term personal play more than a strict STR deal. 

I asked when the other person will retire.  

I'm never going to use your website because I already have personal relationships with people doing that work.

.✅ 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.

I would not borrow from ANY lender I learned of over the internet unless I knwe personally people who had used them. 

- Loss of historical data (for both IRS audits and for personal portfolio tracking.)You should be able to print the general ledger and Balance sheet / income statement for each period.

And always check social media for red flags and I agree with Vince, always meet a person.  

No personal experience with them.