Disclosure I have a small amount in Realtymogul in their Mogul Reit 1 and it pays out slightly less than 8% annualized on a monthly basis, this isnt to say it will always perform but so far it has done that for me however it is highly illiquid and it probably will remain that way. 

And convert that into annual savings

Even with using the lowest cost IRA provider out there the fee for 4 separate accounts is over $600 annually assuming my wife & I open a Roth & traditional each.

Do you know of any banks that offer checkbook HELOCs that don't require withdrawals, have low annual fees, and have no restrictions around how many financed rental properties are in your name?

I'm looking for a property mostly in the Wolf Creek and Fruitdale area since I am looking for a property at $200k tops.

And if you need cash, do a refi of the new property.Using the basis of purchase price when you set it up as a rental is only a disadvantage in that it lessens your annual depreciation allowance. 

Our last round projected a 18-22% return annually over 4 years. 

To not be on VRBO would be suicide, so the the $500 annual fee is not something that can (or should) be avoided.

Make sure they have to give updated business and personal financials once  a quarter or at least semi-annually to annually.

Say your property shows a $5,000 annual profit on paper, once you consider the write-offs like depreciation, mortgage interest, property tax, etc, what kind of tax bill should you expect?