This travel expense is not a business expense related to the property you already own until you have identified the next property you want to buy (once identified, costs are added to the basis mentioned above).

I can help with the financing portion, but I would love to help connect you with an outstanding relator in the area.

It helps to try to build rapport with them to show them you're serious, which you may want to work on since you're relatively young and inexperienced.

For a rule of thumb, replacing a commercial boiler can range anywhere from $20k to $150k, depending on the size, age, and efficiency.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Whether that's through the application/leasing process to communicating with owners and vendors in a timely manner to address anything related to the property. 

Typically with houses of this age - you'll need structural folks to dig and install piers into the soil.

I'm a guy approaching middle-age, living in Chicago.

My main goal is it be able to retire at age 40 from my main job and work entirely on my real estate portfolio.

It appears to be a means to an end and the path of least resistance (somewhat related to number 1).