Asking tenants about their experience, any issues with their units, and the building is imperitive for buying properties. 

Factor in an eviction cost and expectation if needed when you are looking at numbers. 

I realized the grass wasn't greener, and I ended up building back in the Chicago area once again.

Raising the rent depends on multiple factors but most of all is market trends.

I was the first developer to build new on that street.

A building is expected to have a functional roof for example and it will not give you value vs other properties who also have a functional roof. 

Most typically you'd hear this term in commercial leasing where the tenant reconfigures an office space or builds out a retail store/restaurant space.

I'm particularly passionate about about BRRRing and Fix and Flip.Outside of real estate, I enjoy spending time with my wife and kids, being in forests (I love big trees), fishing, building things, and financial independence. 

I haven't set specific targets beyond this initial goal, but I may aim to increase my passive income to $5,000 or $10,000 per month in the future.Current PropertiesI currently have two properties:The Loft:This property is rented out long-term and generates around $300 per month in passive income after HOA and management fees.The loft has approximately $100,000 in equity.The House:This is a brand-new build (2024) that I'm currently occupying through house hacking.I invested $70,000 in the property, which means I have $70,000 in equity.My plan is to convert this property into an Airbnb or long-term rental within the next two years.Short-term rental comps suggest I can earn around $3,500-$4,000 per month, while long-term rental comps indicate I can earn around $3,000-$3,300 per month.Seeking AdviceGiven my upcoming financial situation, I'm seeking advice on the best course of action.

Your taxable income may be more than $150,000 since you have to factor in depreciation.You can potentially consider doing a 1031 exchange.