With my long term rentals here it's fairly simple, you have taxes, HOA fees and insurance but with a short term rental i'm not sure how to handle VRBO fees, vacancy with a short term rental, out of state taxes, etc..Still fairly early in the planning phase but have to start somewhere so any help is appreciated!

HOA can be corrupt, depends on who manages it. 

The only comp, because this is a 1/2 acre property out of city limits with no HOA, was in the same neighborhood and rented for $1600.

Well funded HOA. 

It’s also an odd rental, out of city limits no HOA, and between the two worst houses in the neighborhood (one is vacant and hasn’t been mowed in years, the other runs an mechanic shop out of his yard).

Coming in 2nd, is our HOA, turns out my neighbor hasn't paid his HOA Dues in about 3 years (500/year- total amount due to HOA is 1,600.00)That leaves the 3rd.

And make sure to account for the following expenses (if it applies):1) Mortgage2) Mortgage insurance (PMI or MIP) or FHA Risk base3) Property Taxes4) City Taxes5) HOA (Home Owner’s Association) Dues and Fees and Assessments6) Insurance   a) Property Hazard Insurance   b) Flood Insurance   c) Earthquake Insurance   d) Umbrella Insurance7) Vacancy Rate (usually 8% - the equivalent to one month a year, or 5-6% if multifamily and/or if experienced, if not use 8%)8) Utilities (you’ll have these if your tenant is not covering them and/or during vacancy)   a) Water § Sewer § Garbage   b) Electricity   c) Natural Gas   d) Propane9) General Maintenance (usually 5%)   a) Upkeep § Landscaping   b) Snow removal   c) Repairs   d) New Appliances10) Capital Expenditures (usually 5%, higher is the property is old and obsolete, less if fully rehabbed and all mechanicals and roof are new)11) Property Management (8%, even if you self manage, your time still has value and there might be a time when you'll want to be completely hands off or you'll not be able to do it, vacation, retirement, etc.), including...  

They tend to be slower to appreciate and HOA fees tend to rise faster than rents reducing annual cash flow.

Main thing is research the HOAs. 

I think the two biggest factors you should consider are location and HOA.