Current value of paid off property is roughly 350k , looking to borrow 75k-100k down payment to  purchase a 275k commercial property.

Ignore the $1,250 per month because that's your cost of housing, if you didn't pay that on the home you'd have paid that in rent so that's a non factor. 

At which point our evaluation should rise on the community for closer to $4,000,000.00We've enjoyed digitizing all payments, streamlining service, as well as infilling new homes.

Austin was appreciating faster than non-tech cities.

While the image of yours I found seem to show the main entry to the 2nd floor at ground level, the older the prospective tenant, the less interested they are in a non-ground floor unit. 2) Using another part of the property as storage could limit interest and I could see that as a turn off with folks once they find this out.FYI, the listing I found on realtor.com makes no mention of the tenant not having access the entire property or the basement being used as storage.

There is no issue with eviction for non-payment of rent during the winter in Wisconsin.

The VA will not allow you to make payments during the build process. 

I'm looking to invest between $50k and $75k as the down payment. 

A non-franchised Broker with six agents won't have professional training and resources, so a new agent won't be trained as well and will struggle to get started. 

It's going to be challenging to find another house hack with as low of a monthly payment as you currently have, given the low interest rate.