I may end up selling the lots and going for a rehab mainly due to lack of knowledge and comfort in that area of investment but definitely feel like I could turn the property into some what of a income producer. 

Pete beach, I can get you a list of ones in your purchase area that allow short term rentals then I would recommend to request financials from all the condo associations to ensure no large assessment is coming and all maintenance is up to date with a healthy reserves account.

Top producing agents pretty much have purview to do what they want, those of us in the top 1% of the profession. 

I know companies can produce them but is it worth going to the county to get it?

It will be a lot of fungicide sprays in that area… most of the vineyards in the Hill Country are small for premium production due to high farming costs or are strictly for show.80%+ of Texas grapes are produced up here in the high plains AVA where it’s much easier and cheaper to grow.

Have the income that 100 units produce?

But the listings I see on Zillow and Realtor.com seem awfully steep and not many seem like it'd provide good ROI and a healthy cash-flow.

This is a healthy thing to do whether you are investing or not, but what you should do is keep a notebook for one month.

Good deals don't produce much, if any, passive loss.

Not to mention they use hardly any energy to run and don't produce heat.