That is a tall order, people should expect in some towns your kids can't buy in and its not because of STR it is because the property has a higher value.Now in AZ you have a snowbird issue that complicates your STR market.So this like many real estate issues is local. 

@Remington Lyman please ignore, its complicated...i will post back once we close the deal on what we had to do with zoning etc... many lenders decline to fund the loan as the zone was commercial and fanni and freddi backed lenders would not do commercial zoned properties...

I do not want the hardwired combo (more expensive and complicated to install) - From what I've read, hardwiring is required for multi-family housing, but I don't see that it is for single family residential.

Looks like more complicated circumstance than I expected.

It's the option with the least complications & sets you on the path to FIRE, which is your ultimate goal!

Pricelabs is very complicated.

While the bookkeeping will likely be complicated, is the accounting/taxation on this STR based on 100% STR income/expenses allocated 100% to business and general house expenses (mortgage, utilities, depreciation etc) pro rated between STR/personal residence based on sq footage?  

Based on what I remember, it gets even more complicated if the 401k is from a previous employer.In your case, since Fidelity is declining the account due to the nature of the retirement funds, one option might be to consider rolling over a portion of your 401k into a self-directed IRA, which typically offers more flexibility.

You do need to send in a check with the extension, the irs provides guidelines for calculating the amount.Real estate investing complicates taxes sufficiently that I have found I save way more than I spend by having a CPA who specializes in real estate investor tax returns.

In most cases, neither is warranted.Warning: I am not an attorney, and this can be a complicated topic.