And of course, take advantage of the tax benefits along side my current business income.Viability of the idea?

Private money may be better. 

Quote from @Dan Farsht: I am looking to connect with other hard money lenders in the upper Midwest (our business is currently concentrated in the Greater Milwaukee Area). 

It is the cost of doing business.

Years in business?

If you are apprehensive of the market, and believe it will get worse before it gets better, you might consider going to cash, doing a private loan to a flipper on a project where it would be a screaming deal if you had to foreclose, and taking a look in 9 or 18 months. 

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

., They will be instrumental to your business. 

I almost fell over dead thinking maybe I was going into the wrong business.

Check out the STR forum where you'll find some great information and will see questions and answers from those who have successfully scaled STR businesses.