The garages will have 3% increases year over year once leased.

Low down payment, but you would be increasing the value of the property with your own cash.

Also seems that most brands have limited options for dressers, and those they do have are more concerned with having a trendy MCM look than being functional. 

Would the value of the remodel increase the rents or the selling price that would out weight the cost? 

(make sure you are budgeting for maintenance and management if you plan to use it) Rent will increase over time and your property will continue to appreciate in value. 

Is there a point of contact person/business that handles all home investor concerns (general contractor, engineer, etc.)

It’s concerning as I have a lot of money tied up in this.

Our lot is fenced in and we cannot see where he lives but close enough to be of concern, but we want to stay in the same town until the kids are finished school.So, my question is this, would it make sense to rent our home (roughly $2300-2500/mo. as per real-estate agent claims), with the stipulation that the garage is used for my business AND buy a home nearby?

But I do have some family in Canada that have told me there has been some tax increases to the STR owners to try combat housing issues.

If you know that something major will need replacement in the future, increase the monthly amount you are depositing into your reserve fund.