I took a very high level look at it and the proposal is quite ridiculous.

For example, a higher cap rate indicates a higher potential return, but it also indicates higher levels of risk, which means that the price an investor may be willing to pay is lower.For example: An investor was considering purchasing one of the two properties.Property 1: $100,000 NOI / $1,000,000 Purchase Price = 10% Cap Rate.Property 2: $500,000 NOI / $6,250,000 Purchase Price = 8% Cap RateWhen comparing these two potential purchases, it is safe to assume that Property 1 carries more risk because it has a higher cap rate.

We're both dedicated and hardworking and have the skills to make repairs so a fixer upper is not out of the realm of possibilities. 

It seems as though you have some high level return metrics you are looking for (i.e. 2x multiple would indicate you're looking to double your money during the investment: $50K ----> $100K) so curious what return you are looking to calculate more granularly?

JD said it best - I'm ok leaving some money on the table, as long as the property is performing at a high level.

For me, it added an extra level of security/ protection above the regular homeowners policy (injury, property damage etc). 

I've considered investing in the upper midwest, but as I researched it, there are a few things that give me pause.

If a sponsor is only showing gross or project level returns, I will immediately hit delete.  

If you get a complete fixer upper in bad condition, then the banks won’t loan on it and you will have to go with a hard money or portfolio loan.

Additionally, have to work around the concrete slab/driveway.New plan is to just finish converting the garage and instead of building out, raising the roof enough to get a second level.