We thought about fencing/gating ours and making a community or just simply adding garages if it doesn't get too pricey.

You may be able to sign up with a firm and do remote, ad-hoc work as needed or when you have time. 

This does not even cover more costs to keep improving and adding to the software.

That said, expect to deal with a fair amount of fluff leads.The two best strategies I’ve found are inbound methods: direct mail and Google Ads.Direct mail can be expensive, but it can also yield highly discounted properties.Google Ads, on the other hand, doesn’t require data extraction like calls, direct mail, or texting.

While a detailed log is often sufficient, adding additional documentation can strengthen your record. 

If you're growing your portfolio quickly, the added flexibility can make it worthwhile.

Will be adding that in for sure.. 

I'm looking into HVAC options and will be adding AC as well.

AND with STRs you have no risk of evictions (which can get to be real expensive depending on the area)  and most damages that guests do are covered by insurance (either through the rental platform it was booked through or sometimes the property management firm has added insurance too).As someone that build a large long term rental portfolio here in Illinois (I still have 40+ houses here) and somebody now building a portfolio in tennessee, I would definitely recommend looking at new construction in some of these str areas. 

Furnished and added to the AirBnB circuit for 1 year.