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?  

I'm paying down principle much faster than I would with a 30 year fixed loan and slightly faster than a 15 year fixed loan.It's a bit complicated to explain but you use this loan as your checking account.   

@Carlo D.Maybe it is true for their bank but not for other banks.My wife and I have a (more complicated) trust that owns several LLCs.

I only invite someone to apply if I think I want to rent to them, otherwise I think it is an unnecessary expense for the prospective tenant.

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.

Gas, water, elec are unnecessary.