Our economy is doing very well and Toledo has a very rental-heavy housing culture. 

Unfortunately, I have been stuck for months trying to find appropriate insurance for the vehicle. 

With older homes go heavy on the inspections and know what you’re getting into up front.

We're seeking a 2-family house with parking for at least one vehicle and close to public transportation.

I wouldn't do that, they are not bad actors,  these are C properties with heavy value add which is higher risk, and certainly mistakes were made.

If you drive a vehicle, how much of that $20-50 bucks a month covers gas, insurance, tolls, etc.? 

Airbnbs are huge here as Chicago is very tourist heavy.

Even though they do a lot of the heavy lifting on sourcing and analyzing deals, I would never pull the trigger if I hadn't run the numbers myself.

Now new HOA management is issuing violations, saying No Commercial Vehicles allowed. 

It is very important, no matter the investment vehicle, to do thorough due diligence, ask for track records, know the risks, make sure there is a great deal of transparency and excellent communication with any Sponsor.