I’ve worked for some group home providers where they employ a maintenance worker who handles some of these issues (usually if the have multiple homes in a specific geographic location) and I’ve worked for homes where the handiest employee fixes things and that option doesn’t always have the best outcomes.

For us, the only time we pay contractors upfront is when it is for really specific jobs like full HVAC and full Electrical jobs, and these are somewhat large companies with vans and trucks, so we know that these guys aren't running anywhere with our $3k upfront payment. 

Most Brokers on this site work very specific markets.

Is it from experience of there are tools out there that show numbers on specific areas?

Some were purchased specifically to be MTRs & others were conversions when it made sense.  

Instead:401(k) loans: They’re low-interest, and you’re paying yourself back.Roth rollovers If you can afford the taxes now, this gives future flexibility.Creative financing: I’ve seen clients leverage partnerships or seller financing to limit retirement fund withdrawals.One thing to consider: real estate markets today are vastly different from a decade ago.. so opportunities may require extra creativity.Have you looked into specific deals yet?

Like @John Underwood mentioned, you need to set the expectation of a 5 star review.We're very specific on our messaging automation. 

Are there areas of specific interest? 

Once you know what specifically is stopping you, you can address it directly—whether that means learning more, asking specific questions, or just taking a smaller step forward.Sometimes the biggest hurdle is just narrowing down that fear and facing it head-on.

But for an OOS investor one consideration is access to support, first of all PM & contractors, and you have more choices in the much larger Milwaukee metro area than in a smaller submarket.